L-(+)-Cysteine → HCID 56619774, compound

HRID 1981144Notes

Reaction equation

[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13]I)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:15][C@H:16]([C:19]([OH:21])=[O:20])[CH2:17][SH:18].C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O.NCCSC[C@@H](C(O)=O)N.C(OC(=O)[C@@H]1CCCN1)(C)(C)C.C1(N=C=NC2CCCCC2)CCCCC1>>[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][S:18][CH2:17][C@@H:16]([C:19]([OH:21])=[O:20])[NH2:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 6

HCID 5862L-(+)-Cysteine

HCID 10868Dicyclohexylcarbodiimide

HCID 90495Di-tert-butyl dicarbonate

HCID 99558S-(2-Aminoethyl)-L-cysteine

HCID 6453108L-Proline 1,1-dimethylethyl ester

HCID 11301181Benzyl (2-iodoethyl)carbamate

Product 1

HCID 56619774HCID 56619774, compound

Procedure

S-Benzyloxycarbonylaminoethyl-L-cysteine is prepared from benzyloxycarbonyl-2-iodoethylamine and L-cysteine by the method of H. Lindley (Austral. J. Chem., 12, 296,1959). The α-amino group is protected with tert-butoxycarbonyl using di-tert-butyl dicarbonate. The resulting fully protected S-2-aminoethyl-L-cysteine is condensed with L-proline-tert-butyl ester in the presence of N,N'-dicyclohexylcarbodiimide. This intermediate is readily purified by medium pressure liquid chromatography on silica in ethyl acetate/hexane (1:1).

Workup

customThis intermediate is readily purified by medium pressure liquid chromatography on silica in ethyl acetate/hexane (1:1)

Sources & evidence

ORD record: ord-d9b30692782a43ccb4f4d238bdfb0a25
Source dataset: uspto-grants-1985_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04512979

Reaction notes

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