N-[tert-butoxycarbonyl]-L-serine → HCID 22859485, compound

HRID 1441187Notes

Reaction equation

HRID 1441187 reaction equation
C[O:2][C:3](=[O:11])[C@@H:4]([NH2:10])[CH2:5][CH:6]([CH3:9])[CH:7]=[CH2:8].N(C(OC(C)(C)C)=O)[C@H](C(O)=O)CO>>[NH2:10][C@@H:4]([CH2:5][CH:6]([CH3:9])[CH:7]=[CH2:8])[C:3]([OH:11])=[O:2]

Participants

3

Reactant 2

HCID 98766N-[tert-butoxycarbonyl]-L-serineHCID 53770144HCID 53770144, compound

Product 1

HCID 22859485HCID 22859485, compound

Procedure

Entry No. 47: The 2(S)-amino-4-methyl-5-hexenoic acid methyl ester employed for the preparation of this peptide was obtained by converting Boc-Ser-OH to its corresponding β-lactone by the method of J. C. Vederas et ai., J. Am. Chem. Soc., 107 7105 (1985) and reacting the β-lactone with the organolithium derivative derived from 2-propylene bromide according to the method of D. Seebach and H. Neumann, Chem. Ber., 107, 847 (1974) to give 2(S)-amino-4-methyl-5-hexenoic acid. Subsequent esterification of the latter compound with diazomethane gave the desired corresponding methyl ester.

Workup

  1. customwas obtained

Sources & evidence

ORD record
ord-d028f0593df141b9908c3bb056712261
Source dataset
uspto-grants-1996_03
Patent number
US05502036

Reaction notes

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