Lithium Hydroxide → HCID 178445687, compound

HRID 1717699Notes

Reaction equation

HRID 1717699 reaction equation
[C:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([N:11]([C:28](=[O:40])[C:29]2[CH:34]=[CH:33][C:32]([O:35][C:36]([F:39])([F:38])[F:37])=[CH:31][CH:30]=2)[CH:12]2[C:20]3[C:15](=[CH:16][C:17]([C:21](OCCCC)=[O:22])=[CH:18][CH:19]=3)[CH2:14][CH2:13]2)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-].[NH2:43][C:44]1[NH:48][N:47]=[N:46][N:45]=1>>[C:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([N:11]([C:28](=[O:40])[C:29]2[CH:34]=[CH:33][C:32]([O:35][C:36]([F:39])([F:38])[F:37])=[CH:31][CH:30]=2)[CH:12]2[C:20]3[C:15](=[CH:16][C:17]([C:21]([NH:43][C:44]4[NH:48][N:47]=[N:46][N:45]=4)=[O:22])=[CH:18][CH:19]=3)[CH2:14][CH2:13]2)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 3939Lithium HydroxideHCID 178450644HCID 178450644, compoundHCID 178509299HCID 178509299, compound

Product 1

HCID 178445687HCID 178445687, compound

Procedure

Butyl 1-{(trans-4-tert-butylcyclohexyl)[4-(trifluoromethoxy)benzoyl]amino}indane-5-carboxylate, enantiomer A (50 mg) or enantiomer B (70 mg), was saponified with aqueous LiOH and then coupled to 5-amino tetrazole following the procedure described (Step D., Example 1/2) to give 1-{(trans-4-tert-butylcyclohexyl)[4-(trifluoromethoxy)benzoyl]amino}-N-1H-tetrazol-5-ylindane-5-carboxamide. Enantiomer A: HPLC/MS: m/z=571.2 (M+1), Rt=2.65 min. 1H NMR (DMSO-d6): δ 12.34 (1H, br s), 7.95 (1H, s), 7.90 (1H, d, J=8.0 Hz), 7.52 (2H, d, J=8.0 Hz), 7.44 (2H, d, J=8.0 Hz), 7.35 (1H, d, J=8.0 Hz), 5.05 (1H, m), 3.35 (1H, m), 3.15 (1H, m), 2.96 (1H, m), 2.55 (1H, m), 2.36 (1H, m), 2.12 (1H, m), 1.77 (6H, m), 0.99 (1H, m), 0.84 (1H, m), 0.79 (9H, s). Enantiomer B: HPLC/MS and 1H NMR (DMSO-d6) are identical to those of enantiomer A.

Sources & evidence

ORD record
ord-11ed16ef011347d98e138216b2c18047
Source dataset
uspto-grants-2010_09
Patent number
US07803951B2

Reaction notes

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