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3850-40-6

3850-40-6 Structure

3850-40-6 Structure
IdentificationBack Directory
[Name]

Serine, N-[(1,1-dimethylethoxy)carbonyl]- (9CI)
[CAS]

3850-40-6
[Synonyms]

Boc-DL-serine
(tert-Butoxycarbonyl)serine
(Tert-Butoxy)Carbonyl DL-Ser-OH
Serine,N-[(1,1-diMethylethoxy)carbonyl]-
Serine, N-[(1,1-dimethylethoxy)carbonyl]- (9CI)
3-hydroxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
[Molecular Formula]

C8H15NO5
[MDL Number]

MFCD00190830
[MOL File]

3850-40-6.mol
[Molecular Weight]

205.21
Chemical PropertiesBack Directory
[Boiling point ]

385.1±37.0 °C(Predicted)
[density ]

1.240±0.06 g/cm3(Predicted)
[storage temp. ]

2-8°C
[pka]

3.62±0.10(Predicted)
[Appearance]

White to off-white Solid
Safety DataBack Directory
[Symbol(GHS) ]

GHS hazard pictograms
GHS07
[Signal word ]

Warning
[Hazard statements ]

H335-H319-H315
[Precautionary statements ]

P264-P280-P305+P351+P338-P337+P313P-P264-P280-P302+P352-P321-P332+P313-P362
Spectrum DetailBack Directory
[Spectrum Detail]

Serine, N-[(1,1-dimethylethoxy)carbonyl]- (9CI)(3850-40-6)1HNMR
Hazard InformationBack Directory
[Synthesis]

D-Serine

312-84-5

Di-tert-butyl dicarbonate

24424-99-5

BOC-L-Serine

3262-72-4

Sodium hydroxide (8.4 g, 0.110 mol) was dissolved in water (53 mL) and stirred at room temperature until completely dissolved, followed by cooling to 5-10 °C. D-serine (10.5 g, 0.100 mol) and di-tert-butyl dicarbonate (26.2 g, 0.120 mol) were slowly added while the temperature was maintained at ≤10 °C. The reaction mixture was gradually heated to 30-35 °C and the reaction was stirred at this temperature for 20 hours. Upon completion of the reaction, an aqueous solution of BOC-L-serine was obtained (yield based on 100%, HPLC purity 99.1%, chiral purity 99.4%). This aqueous solution can be used directly in the subsequent synthesis steps without further purification.

[References]

[1] Journal of the American Chemical Society, 1994, vol. 116, # 18, p. 8402 - 8403
[2] Journal of the American Chemical Society, 2008, vol. 130, # 7, p. 2351 - 2364
[3] Advanced Synthesis and Catalysis, 2016, vol. 358, # 1, p. 34 - 40
[4] Patent: CN104030943, 2016, B. Location in patent: Paragraph 0095; 0096
[5] Beilstein Journal of Organic Chemistry, 2014, vol. 10, p. 1114 - 1120
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