4-{(S)-2-[(4-Benzyloxycarbonylmethoxy-7-methyl-naphthalene-2-carbonyl)-amino]-4-tert-butoxycarbonyl-butyryl}-piperazine-1-carboxylic acid butyl ester → 4-{(S)-4-tert-Butoxycarbonyl-2-[(4-carboxymethoxy-7-methyl-naphthalene-2-carbonyl)-amino]-butyryl}-piperazine-1-carboxylic acid butyl ester

HRID 1185507Notes

Reaction equation

HRID 1185507 reaction equation
[CH2:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:51])[C@@H:15]([NH:25][C:26]([C:28]2[CH:37]=[C:36]([O:38][CH2:39][C:40]([O:42]CC3C=CC=CC=3)=[O:41])[C:35]3[C:30](=[CH:31][C:32]([CH3:50])=[CH:33][CH:34]=3)[CH:29]=2)=[O:27])[CH2:16][CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:10][CH2:9]1)=[O:7])[CH2:2][CH2:3][CH3:4]>C(OCC)(=O)C.[Pd]>[CH2:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:51])[C@@H:15]([NH:25][C:26]([C:28]2[CH:37]=[C:36]([O:38][CH2:39][C:40]([OH:42])=[O:41])[C:35]3[C:30](=[CH:31][C:32]([CH3:50])=[CH:33][CH:34]=3)[CH:29]=2)=[O:27])[CH2:16][CH2:17][C:18]([O:20][C:21]([CH3:22])([CH3:24])[CH3:23])=[O:19])[CH2:10][CH2:9]1)=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 1

HCID 686000914-{(S)-2-[(4-Benzyloxycarbonylmethoxy-7-methyl-naphthalene-2-carbonyl)-amino]-4-tert-butoxycarbonyl-butyryl}-piperazine-1-carboxylic acid butyl ester

Product 1

HCID 685984354-{(S)-4-tert-Butoxycarbonyl-2-[(4-carboxymethoxy-7-methyl-naphthalene-2-carbonyl)-amino]-butyryl}-piperazine-1-carboxylic acid butyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 710 mg 4-{(S)-2-[(4-Benzyloxycarbonylmethoxy-7-methyl-naphthalene-2-carbonyl)-amino]-4-tert-butoxycarbonyl-butyryl}-piperazine-1-carboxylic acid butyl ester in 15 ml ethyl acetate were added 200 mg Pd/C (10%) and the suspension stirred under an atmosphere of hydrogen (3 bar) for 1 h. Then the reaction mixture was filtrated over a plug of Celite®, washed with ethyl acetate and concentrated. Yield: 670 mg colorless oil.

Workup

  1. filtrationThen the reaction mixture was filtrated over a plug of Celite®
  2. washwashed with ethyl acetate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-08354e10ede04669b95d4adbdd7bafbe
Source dataset
uspto-grants-2014_03
Patent number
US08669266B2

Reaction notes

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