Formamide → HCID 67097705, compound

HRID 2078651Notes

Reaction equation

HRID 2078651 reaction equation
C[O-].[Na+].[C:4]([O:8][C:9]([N:11]([CH2:45][C@H:46]([OH:53])[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)[CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][C:23]([C:26]([NH:28][S:29]([CH2:32][CH2:33][C:34]([O:36]C)=O)(=[O:31])=[O:30])=[O:27])=[C:22]([O:38][CH:39]3[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]3)[CH:21]=2)=[CH:16][CH:15]=1)=[O:10])([CH3:7])([CH3:6])[CH3:5].C([NH2:56])=O>>[NH2:56][C:34](=[O:36])[CH2:33][CH2:32][S:29]([NH:28][C:26]([C:23]1[CH:24]=[CH:25][C:20]([C:17]2[CH:18]=[CH:19][C:14]([CH2:13][CH2:12][N:11]([CH2:45][C@H:46]([OH:53])[C:47]3[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=3)[C:9](=[O:10])[O:8][C:4]([CH3:5])([CH3:6])[CH3:7])=[CH:15][CH:16]=2)=[CH:21][C:22]=1[O:38][CH:39]1[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]1)=[O:27])(=[O:30])=[O:31]

Participants

4

Reactant 3

HCID 713FormamideHCID 10942334Sodium MethoxideHCID 67097757HCID 67097757, compound

Product 1

HCID 67097705HCID 67097705, compound

Conditions

Temperature
60 °C

Procedure

Sodium methoxide (38.1 mg) was added to a solution of methyl 3-[[[[4′-[2-[(tert-butoxycarbonyl)[(2R)-2-hydroxy-2-phenylethyl]amino]ethyl]-3-(cyclohexyloxy)-4-biphenylyl]carbonyl]amino]sulfonyl]propanoate (125 mg) in formamide (2.0 ml) at room temperature. The mixture was stirred for 1.5 hours at 60° C. The product was extracted with ethyl acetate. The combined extracts were washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by silica gel column chromatography to give tert-butyl [2-[4′-[[[(3-amino-3-oxopropyl)sulfonyl]amino]carbonyl]-3′-(cyclohexyloxy)-4-biphenylyl]ethyl][(2R)-2-hydroxy-2-phenylethyl]carbamate (22.0 mg).

Workup

  1. extractionThe product was extracted with ethyl acetate
  2. washThe combined extracts were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-91026e816cb645919cfdcde1548e7ab9
Source dataset
uspto-grants-2011_04
Patent number
US07928264B2

Reaction notes

Loading…