Ethanol → HCID 69356611, compound

HRID 852671Notes

Reaction equation

HRID 852671 reaction equation
[CH2:1]([C@H:8]([NH:24][C:25](=[O:41])[C:26]1[CH:31]=[C:30]([N:32]2[CH2:36][CH2:35][CH2:34][C:33]2=[O:37])[CH:29]=[C:28]([N+:38]([O-])=O)[CH:27]=1)[C@H:9]([OH:23])[CH2:10][NH:11][C@H:12]([C:14](=[O:22])[NH:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)[CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCO>[Pd].O>[NH2:38][C:28]1[CH:27]=[C:26]([CH:31]=[C:30]([N:32]2[CH2:36][CH2:35][CH2:34][C:33]2=[O:37])[CH:29]=1)[C:25]([NH:24][C@@H:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C@H:9]([OH:23])[CH2:10][NH:11][C@H:12]([C:14](=[O:22])[NH:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)[CH3:13])=[O:41]

Participants

5

Reactant 2

HCID 702EthanolHCID 69356742HCID 69356742, compound

Product 1

HCID 69356611HCID 69356611, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of N-[(1S,2R)-1-benzyl-3-((S)-1-cyclohexylcarbamoyl-ethylamino)-2-hydroxy-propyl]-3-nitro-5-(2-oxo-pyrrolidin-1-yl)-benzamide (E62) (40 mg, 0.07 mmol, 1 equiv), 10% Pd on charcoal (50% wet, 10 mg, 12.5% w/w), NH4COOH (55 mg, 0.90 mmol, 13 equiv), EtOH (5 ml) and H2O (2.5 ml) was stirred at 50° C. for 2 h, cooled to room temperature and the catalyst was filtered off through a pad of celite. Most of the EtOH was removed in vacuo and the residue was partitioned between AcOEt and saturated aqueous NaHCO3 solution. The aqueous phase was extracted with AcOEt. The combined organic phases were dried over MgSO4 and concentrated in vacuo. The residue was triturated with Et2O to give 3-amino-N-[(1S,2R)-1-benzyl-3-((S)-1-cyclohexylcarbamoyl-ethylamino)-2-hydroxypropyl]-5-(2-oxo-pyrrolidin-1-yl)-benzamide (E63) (15 mg, 38%) as a pale yellow solid. [M+H]+=536.1 RT-=2.27 min

Workup

  1. temperaturecooled to room temperature
  2. filtrationthe catalyst was filtered off through a pad of celite
  3. customMost of the EtOH was removed in vacuo
  4. customthe residue was partitioned between AcOEt and saturated aqueous NaHCO3 solution
  5. extractionThe aqueous phase was extracted with AcOEt
  6. dry with materialThe combined organic phases were dried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was triturated with Et2O

Sources & evidence

ORD record
ord-df585a8ef43745b1abc288daf2bbd4d5
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

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