Methanol → HCID 54169572, compound

HRID 1739581Notes

Reaction equation

HRID 1739581 reaction equation
C[O:2][C:3](=[O:47])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([NH:20][C:21]([O:23][CH:24]4[CH2:28][CH2:27][CH2:26][CH2:25]4)=[O:22])[CH:18]=3)[N:13]([C:29](=[O:44])[NH:30][CH:31]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH:12]=2)=[C:6]([O:45][CH3:46])[CH:5]=1.O1CCCC1.CO.O.[OH-].[Li+]>O>[CH:31]([NH:30][C:29]([N:13]1[C:14]2[C:19](=[CH:18][C:17]([NH:20][C:21]([O:23][CH:24]3[CH2:25][CH2:26][CH2:27][CH2:28]3)=[O:22])=[CH:16][CH:15]=2)[C:11]([CH2:10][C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:47])=[O:2])=[CH:5][C:6]=2[O:45][CH3:46])=[CH:12]1)=[O:44])([C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 54080357HCID 54080357, compound

Product 1

HCID 54169572HCID 54169572, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 4-[1-(benzhydryl-carbamoyl)-5-(cyclopentyloxycarbonyl)amino-1H-indol-3-ylmethyl]-3-methoxy-benzoic acid methylester (0.58 grams, 0.92 mmol) in 2:2:1 ratio of tetrahydrofuran:methanol:water (30 mL) was added lithium hydroxide monohydrate (0.19 grams, 4.50 mmol). The resulting solution was stirred at room temperature for 12 hours and then concentrated in vacuo. The crude product was treated with 1 M hydrochloric acid (aq), and the resulting precipitate collected via filtration to give 4-[1-(benzhydryl-carbamoyl)-5-(cyclopentyloxycarbonyl)amino-1H-indol-3-ylmethyl]-3-methoxy-benzoic acid (0.514 grams, 91% yield).

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe crude product was treated with 1 M hydrochloric acid (aq)
  3. filtrationthe resulting precipitate collected via filtration

Sources & evidence

ORD record
ord-e584a0814d7e46fb8b732e36b2e27207
Source dataset
uspto-grants-1999_10
Patent number
US05965745

Reaction notes

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