(2S)-4-aminobutane-1,2-diol → (4'S,5'R)-6''-chloro-4'-(3-chloro-2-fluorophenyl)-N-[(3S)-3,4-dihydroxybutyl]-1'-[(1R,2S)-2-hydroxy-1,2-diphenylethyl]-4,4-dimethyl-2''-oxo-1'',2''-dihydrodispiro[cyclohexane-1,2'-pyrrolidine-3',3''-indole]-5'-carboxamide

HRID 470664Notes

Reaction equation

HRID 470664 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C@@:6]3([C:19]4([CH2:24][CH2:23][C:22]([CH3:26])([CH3:25])[CH2:21][CH2:20]4)[N:18]4[C@@H:13]([C:14](=[O:39])[O:15][C@@H:16]([C:33]5[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=5)[C@H:17]4[C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[C@@H:12]3[C:40]3[CH:45]=[CH:44][CH:43]=[C:42]([Cl:46])[C:41]=3[F:47])[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.[NH2:48][CH2:49][CH2:50][C@H:51]([OH:54])[CH2:52][OH:53]>>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]3([C@@H:12]([C:40]4[CH:45]=[CH:44][CH:43]=[C:42]([Cl:46])[C:41]=4[F:47])[C@H:13]([C:14]([NH:48][CH2:49][CH2:50][C@H:51]([OH:54])[CH2:52][OH:53])=[O:39])[N:18]([C@H:17]([C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)[C@@H:16]([OH:15])[C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=4)[C:19]43[CH2:20][CH2:21][C:22]([CH3:26])([CH3:25])[CH2:23][CH2:24]4)[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 55281176(2S)-4-aminobutane-1,2-diolHCID 70872025(3'S,4'R,7'S,8'S,8a'R)-6''-chloro-8'-(3-chloro-2-fluorophenyl)-4,4-dimethyl-3',4'-diphenyl-3',4',8',8a'-tetrahydro-1'H-dispiro[cyclohexane-1,6'-pyrrolo[2,1-c][1,4]oxazine-7',3''-indole]-1',2''(1''H)-dione

Product 1

HCID 68309385(4'S,5'R)-6''-chloro-4'-(3-chloro-2-fluorophenyl)-N-[(3S)-3,4-dihydroxybutyl]-1'-[(1R,2S)-2-hydroxy-1,2-diphenylethyl]-4,4-dimethyl-2''-oxo-1'',2''-dihydrodispiro[cyclohexane-1,2'-pyrrolidine-3',3''-indole]-5'-carboxamideYield 55%

Procedure

The compound (1.01 g, 1.51 mmol) obtained in Step 1 of Example 1 and (2S)-4-aminobutane-1,2-diol (WO2007/011162) (475 mg, 4.53 mmol) were used as starting materials and treated in the same way as in Step 2 of Example 1 to give 644 mg (55%) of the title compound as a colorless amorphous solid.

Workup

  1. additiontreated in the same way as in Step 2 of Example 1

Sources & evidence

ORD record
ord-0d459261e9584b91bb35e4cefddac3f4
Source dataset
uspto-grants-2014_01
Patent number
US08629133B2

Reaction notes

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