Neopentyl alcohol → HCID 68914363, compound

HRID 732677Notes

Reaction equation

HRID 732677 reaction equation
CC(C)(C)C[OH:4].[CH:7]([C:9]1[CH:55]=[CH:54][C:12]([O:13][C:14]2[CH:53]=[CH:52][C:17]([C:18]([N:20]3[CH2:24][C@H:23]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[C@@H:22]([CH2:31][N:32]([C@@H:40]([C:42]4[C:51]5[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=5)[CH:45]=[CH:44][CH:43]=4)[CH3:41])[C:33](=[O:39])[O:34][C:35]([CH3:38])([CH3:37])[CH3:36])[CH2:21]3)=[O:19])=[CH:16][CH:15]=2)=[CH:11][CH:10]=1)=[O:8].P([O-])(O)(O)=O.[K+].CC(=CC)C.Cl([O-])=O.[Na+]>>[C:35]([O:34][C:33]([N:32]([CH2:31][C@@H:22]1[C@@H:23]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:24][N:20]([C:18]([C:17]2[CH:16]=[CH:15][C:14]([O:13][C:12]3[CH:54]=[CH:55][C:9]([C:7]([OH:4])=[O:8])=[CH:10][CH:11]=3)=[CH:53][CH:52]=2)=[O:19])[CH2:21]1)[C@@H:40]([C:42]1[C:51]2[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=2)[CH:45]=[CH:44][CH:43]=1)[CH3:41])=[O:39])([CH3:38])([CH3:37])[CH3:36]

Participants

6

Reactant 5

HCID 6404Neopentyl alcoholHCID 105532-Methyl-2-buteneHCID 516951Monobasic potassium phosphateHCID 23668197Sodium ChloriteHCID 86628544tert-butyl ({(3R,4S)-1-[4-(4-formylphenoxy)benzoyl]-4-phenylpyrrolidin-3-yl}methyl)[(1R)-1-(1-naphthyl)ethyl]carbamate

Product 1

HCID 68914363HCID 68914363, compound

Procedure

A 4 ml 2,2-dimethylpropanol/1 ml water mixed solution of 286 mg of tert-butyl ({(3R,4S)-1-[4-(4-formylphenoxy)benzoyl]-4-phenylpyrrolidin-3-yl}methyl)[(1R)-1-(1-naphthyl)ethyl]carbamate was mixed with 892 mg of potassium dihydrogenphosphate, 1 ml of 2-methyl-2-butene and 394 mg of sodium chlorite and stirred at room temperature for 3 hours. By carrying out its work-up and purification in the standard method, 293 mg of 4-(4-{[(3R,4S)-3-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpyrrolidin-1-yl]carbonyl}phenoxy)benzoic acid was obtained as a pale yellow oily substance. EP: 671. (3) By carrying out the Boc-elimination reaction in the same manner as in Example 5,4-(4-{[(3S,4S)-3-({[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpyrrolidin-1-yl]carbonyl}phenoxy)benzoic acid hydrochloride was produced from 4-(4-{[(3R,4S)-3-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpyrrolidin-1-yl]carbonyl}phenoxy)benzoic acid.

Workup

  1. customits work-up and purification in the standard method

Sources & evidence

ORD record
ord-c2d469f8c1f14e34b2c1d7cb8458f797
Source dataset
uspto-grants-2009_09
Patent number
US07585886B2

Reaction notes

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