Hydrochloric Acid → N-[(R)-1-ethoxycarbonyl-2pentylthioethyl]-alanyl-(S)-prolyl-(S)-proline t-butyl ester

HRID 476986Notes

Reaction equation

HRID 476986 reaction equation
[CH2:1]([O:3][C:4]([C@@H:6]([NH:14][C@H:15]([C:17]([OH:19])=O)[CH3:16])[CH2:7][S:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])=[O:5])[CH3:2].Cl.[C:21]([O:25][C:26](=[O:39])[C@@H:27]1[CH2:31][CH2:30][CH2:29][N:28]1[C:32](=[O:38])[C@@H:33]1[CH2:37][CH2:36][CH2:35][NH:34]1)([CH3:24])([CH3:23])[CH3:22]>>[C:21]([O:25][C:26](=[O:39])[C@@H:27]1[CH2:31][CH2:30][CH2:29][N:28]1[C:32](=[O:38])[C@@H:33]1[CH2:37][CH2:36][CH2:35][N:34]1[C:17](=[O:19])[C@H:15]([CH3:16])[NH:14][C@H:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:7][S:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])([CH3:24])([CH3:22])[CH3:23]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 15595892N-[(R)-1-ethoxycarbonyl-2-pentylthioethyl]-alanineHCID 15598548HCID 15598548, compound

Product 1

HCID 70385519N-[(R)-1-ethoxycarbonyl-2pentylthioethyl]-alanyl-(S)-prolyl-(S)-proline t-butyl ester

Procedure

Following the general procedure of Example 27, the title compound was prepared as a colorless oil from 700 mg of the β-isomer of N-[(R)-1-ethoxycarbonyl-2-pentylthioethyl]-alanine prepared in Reference Example 30 and 730 mg of the hydrochloride of (S)-prolyl-(S)-proline t-butyl ester prepared in Reference Example 28. Yield 930 mg.

Workup

  1. customprepared in Reference Example 28

Sources & evidence

ORD record
ord-2b1c29ed82014c9ebca5f22dec9db1d2
Source dataset
uspto-grants-1989_12
Patent number
US04886813

Reaction notes

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