(3R)-N-(benzyloxy)-6-cyclohexyl-3-{4-[(isopropylamino)methyl]-1,3-oxazol-2-yl}hexanamide → (3R)-6-cyclohexyl-N-hydroxy-3-{4-[(isopropylamino)methyl]-1,3-oxazol-2-yl}hexanamide

HRID 2084443Notes

Reaction equation

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

Participants

Conditions

Temperature: 43 °C

Procedure

A solution of (3R)-N-(benzyloxy)-6-cyclohexyl-3-{4-[(isopropylamino)methyl]-1,3-oxazol-2-yl}hexanamide (preparation 157) (85 mg, 0.20 mmol) in EtOH (5 ml) was treated with HCO2NH4 (63 mg, 1.00 mmol) and Pd(OH)2 (20 mg) and the reaction mixture heated at 43° C. for 18 hours. 2 further portions of HCO2NH4 (30 mg+30 mg) and Pd(OH)2 (10 mg+30 mg) were added over a period of 4 hours. The catalyst was filtered off and washed with EtOH. The solvent was removed under reduced pressure. The crude material was purified on a silica column eluting with DCM:MeOH:NH3 (90:10:1) to afford the title compound.

Workup

filtrationThe catalyst was filtered off
washwashed with EtOH
customThe solvent was removed under reduced pressure
customThe crude material was purified on a silica column
washeluting with DCM:MeOH:NH3 (90:10:1)

Sources & evidence

ORD record: ord-e7208fa30a254ccea17379c0d53a4c81
Source dataset: uspto-grants-2004_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06716861B2

Reaction notes

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