Ammonium Chloride → HCID 178508038, compound

HRID 491881Notes

Reaction equation

HRID 491881 reaction equation
[CH2:1]([O:8][C:9]([C@H:11]1[CH2:16][CH2:15][C@@H:14]([N:17]([CH2:47][CH2:48][O:49][CH2:50][C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[C:18](=[O:46])[CH2:19][CH2:20][C@H:21]([NH:28][CH2:29][C:30]2[C:35]([N+:36]([O-])=O)=[CH:34][N:33]=[C:32]([O:39][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[CH:31]=2)[CH:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH4+].[Cl-]>CO.[Zn]>[CH2:1]([O:8][C:9]([C@H:11]1[CH2:12][CH2:13][C@@H:14]([N:17]([C:18](=[O:46])[CH2:19][CH2:20][C@H:21]([NH:28][CH2:29][C:30]2[C:35]([NH2:36])=[CH:34][N:33]=[C:32]([O:39][C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=3)[CH:31]=2)[CH:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[CH2:47][CH2:48][O:49][CH2:50][C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[CH2:15][CH2:16]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 178520644HCID 178520644, compound

Product 1

HCID 178508038HCID 178508038, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

Zinc dust (21.4 g, 330 mmol) was carefully added into a solution of 4-{(2-benzyloxy-ethyl)-[4-[(5-nitro-2-phenoxy-pyridin-4-ylmethyl)-amino]-4-(S)-(tetrahydro-pyran-4-yl)-butyryl]-amino}-cis-cyclohexanecarboxylic acid benzyl ester (1.85 g, 2.4 mmol) and NH4Cl (2.6 g, 48 mmol) in MeOH (300 mL). The resulting mixture was refluxed 4 hours. The MeOH was removed before EtOAc (300 mL) was added. The resulting solution washed with aq. NaHCO3 and aq. NaCl. The organic layer was dried with MgSO4, filtered, and evaporated to yield 4-[[4-[(5-amino-2-phenoxy-pyridin-4-ylmethyl)-amino]-4-(S)-(tetrahydro-pyran-4-yl)-butyryl]-(2-benzyloxy-ethyl)-amino]-cis-cyclohexanecarboxylic acid benzyl ester as a light brown oil.

Workup

  1. temperatureThe resulting mixture was refluxed 4 hours
  2. customThe MeOH was removed before EtOAc (300 mL)
  3. additionwas added
  4. washThe resulting solution washed with aq. NaHCO3 and aq. NaCl
  5. dry with materialThe organic layer was dried with MgSO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-9d2cf31b9e9a463ebce8e9329f2febef
Source dataset
uspto-grants-2009_05
Patent number
US07531545B2

Reaction notes

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