Ethyl 2-(pyrrolidin-2-yl)acetate → N--BOC-L-lysyl-(S)-2-pyrrolidineacetic acid ethyl ester

HRID 979837Notes

Reaction equation

HRID 979837 reaction equation
[C:1]([NH:8][C@H:9]([C:15]([OH:17])=O)[CH2:10][CH2:11][CH2:12][CH2:13][NH2:14])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH2:18]([O:20][C:21](=[O:28])[CH2:22][CH:23]1[CH2:27][CH2:26][CH2:25][NH:24]1)[CH3:19]>>[CH2:18]([O:20][C:21](=[O:28])[CH2:22][C@@H:23]1[CH2:27][CH2:26][CH2:25][N:24]1[C:15](=[O:17])[C@H:9]([CH2:10][CH2:11][CH2:12][CH2:13][NH2:14])[NH:8][C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2])[CH3:19]

Participants

3

Reactant 2

HCID 336545Ethyl 2-(pyrrolidin-2-yl)acetateHCID 2733284epsilon-tert-Butyloxycarbonyl-lysine

Product 1

HCID 53706975N--BOC-L-lysyl-(S)-2-pyrrolidineacetic acid ethyl ester

Procedure

N-α-CBZ, N- -BOC-L-lysine and ethyl-2-pyrrolidineacetate are condensed by the procedure of Example 1, Step C to give N-α-CBZ, N- -BOC-L-lysyl-(S)-2-pyrrolidine acetic acid ethyl ester. The N-α-CBZ group is removed by hydrogenolysis in ethanol containing one equivalent of acetic acid over 10% palladium on charcoal utilizing the procedure of P. G. Katsoyannis and G. P. Schwartz, Methods in Enzymology, 47, 546 (1974), to give N- -BOC-L-lysyl-(S)-2-pyrrolidineacetic acid ethyl ester.

Workup

  1. customcondensed by the procedure of Example 1, Step C

Sources & evidence

ORD record
ord-8419f80b7dd44c5daf578aa5c26a443c
Source dataset
uspto-grants-1987_01
Patent number
US04634716

Reaction notes

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