HCID 86722964, compound → HCID 86722965, compound

HRID 1404360Notes

Reaction equation

HRID 1404360 reaction equation
C([O:8][C:9](=[O:33])[CH2:10][N:11]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH:12]1[CH2:17][CH2:16][CH:15]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:14][CH2:13]1)C1C=CC=CC=1>CO.[OH-].[Pd+2].[OH-]>[C:29]([O:28][C:26]([N:11]([CH2:10][C:9]([OH:33])=[O:8])[CH:12]1[CH2:17][CH2:16][CH:15]([NH:18][C:19]([O:21][C:22]([CH3:24])([CH3:23])[CH3:25])=[O:20])[CH2:14][CH2:13]1)=[O:27])([CH3:32])([CH3:30])[CH3:31]

Participants

4

Reactant 1

HCID 86722964HCID 86722964, compound

Product 1

HCID 86722965HCID 86722965, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A solution of [tert-Butoxycarbonyl-(4-tert-butoxycarbonylamino-cyclohexyl)-amino]-acetic acid benzyl ester (0.277 g, 0.599 mmol) in methanol (6 mL) was purged with argon for 5 min. Palladium hydroxide (20%, 0.053 g) was added, the flask evacuated, and the reaction stirred under a H2 atmosphere for 19 hr. The reaction was filtered through a Celite-plugged filter frit, washed with methanol and DCM, and concentrated. The crude product was carried forward without purification. ESI-MS m/z 395 (M+Na)+.

Workup

  1. customthe flask evacuated
  2. filtrationThe reaction was filtered through a Celite-plugged filter frit
  3. washwashed with methanol and DCM
  4. concentrationconcentrated
  5. customThe crude product was carried forward without purification

Sources & evidence

ORD record
ord-bbdca7c54c3b48f08cdcbfa16b1fc0eb
Source dataset
uspto-grants-2014_12
Patent number
US08912169B2

Reaction notes

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