Sodium Hydroxide → HCID 70067562, compound

HRID 1981410Notes

Reaction equation

HRID 1981410 reaction equation
[C:1]([NH:9][C@@H:10]([CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[CH:11]([OH:43])[CH2:12][N:13]([C:33]([O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:34])[C@H:14]([C:16]([N:18]1[CH2:32][CH2:31][CH2:30][C@H:19]1[C:20]([O:22]CC1C=CC=CC=1)=[O:21])=[O:17])[CH3:15])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>>[C:1]([NH:9][C@@H:10]([CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[CH:11]([OH:43])[CH2:12][N:13]([C:33]([O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:34])[C@H:14]([C:16]([N:18]1[CH2:32][CH2:31][CH2:30][C@H:19]1[C:20]([OH:22])=[O:21])=[O:17])[CH3:15])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 131714200HCID 131714200, compound

Product 1

HCID 70067562HCID 70067562, compound

Procedure

(3S)-1-[N-[3-(Benzoylamino)-2-hydroxy-4-phenylbutyl]-N-[(phenylmethoxy)carbonyl]-L-alanyl]-L-proline, phenylmethyl ester from Example 1 (g) is treated with sodium hydroxide to give (3S)-1-[N-[3-(benzoylamino)-2-hydroxy-4-phenylbutyl]-N-[(phenylmethoxy)carbonyl]-L-alanyl]-L-proline. Treatment with the reagent listed below in Col. I gives the N-protected product shown in Col. II. Removal of the N-protecting group by hydrogenolysis with palladium on carbon catalyst in the presence of hydrochloric acid gives the product shown in Col. III. ##STR183##

Sources & evidence

ORD record
ord-5f11f13547eb4834aea7e5ef07ea681e
Source dataset
uspto-grants-1985_04
Patent number
US04514391

Reaction notes

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