Hydrochloric Acid → HCID 69457066, compound

HRID 1351969Notes

Reaction equation

HRID 1351969 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([O:34][Si](CC)(CC)CC)[CH2:16][NH:17][C@H:18]([CH3:33])[CH2:19][C:20]2[C:28]3[C:23](=[C:24]([C:29]([O:31]C)=[O:30])[CH:25]=[CH:26][CH:27]=3)[NH:22][CH:21]=2)=[CH:11][C:10]=1[NH:42][S:43]([CH3:46])(=[O:45])=[O:44])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].Cl>CO.O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([OH:34])[CH2:16][NH:17][C@H:18]([CH3:33])[CH2:19][C:20]2[C:28]3[C:23](=[C:24]([C:29]([OH:31])=[O:30])[CH:25]=[CH:26][CH:27]=3)[NH:22][CH:21]=2)=[CH:11][C:10]=1[NH:42][S:43]([CH3:46])(=[O:44])=[O:45])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 69457519HCID 69457519, compound

Product 1

HCID 69457066HCID 69457066, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of methyl 3-[(2R)-2-({(2R)-2-{4-(benzyloxy)-3-[(methylsulfonyl)amino]phenyl}-2-[(triethylsilyl)oxy]ethyl}amino)propyl]-1H-indole-7-carboxylate (400 mg, 0.601 mmol) in methanol (20 ml) is added a solution of potassium hydroxide (336 mg, 6.01 mmol) in water (2.0 ml), and the mixture is stirred at 40° C. for 9 hours. The reaction solution is neutralized with 1N hydrochloric acid at 0° C., and thereto is added a pH standard solution (pH 6.8, 5.0 ml). The resultant is purified by reversed phase column (octadecylsilyl, water/methanol 95/5→40/60) to give the title compound (296 mg, yield: 92%).

Workup

  1. customThe resultant is purified by reversed phase column (octadecylsilyl, water/methanol 95/5→40/60)

Sources & evidence

ORD record
ord-bd0904cd21844f8fb1085a03b46c5539
Source dataset
uspto-grants-2007_05
Patent number
US07217724B2

Reaction notes

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