Lithium Hydroxide → HCID 178445688, compound

HRID 1717701Notes

Reaction equation

[C:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([N:11]([C:28](=[O:41])[CH2:29][C:30]2[CH:35]=[CH:34][C:33]([O:36][C:37]([F:40])([F:39])[F:38])=[CH:32][CH:31]=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-].[NH2:44][C:45]1[NH:49][N:48]=[N:47][N:46]=1>>[C:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([N:11]([C:28](=[O:41])[CH2:29][C:30]2[CH:35]=[CH:34][C:33]([O:36][C:37]([F:40])([F:39])[F:38])=[CH:32][CH:31]=2)[CH:12]2[C:20]3[C:15](=[CH:16][C:17]([C:21]([NH:44][C:45]4[NH:49][N:48]=[N:47][N:46]=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

Reactant 3

HCID 3939Lithium Hydroxide

HCID 178450646HCID 178450646, compound

HCID 178509299HCID 178509299, compound

Product 1

HCID 178445688HCID 178445688, compound

Procedure

Butyl 1-((trans-4-tert-butylcyclohexyl){[4-(trifluoromethoxy)phenyl]acetyl}amino)indane-5-carboxylate, enantiomer A (55 mg) or enantiomer B (45 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)phenyl]acetyl}amino)-N-1H-tetrazol-5-ylindane-5-carboxamide. Enantiomer A: HPLC/MS: m/z=585.2 (M+1), Rt=2.75 min. 1H NMR (DMSO-d6): δ 12.30 (1H, br s), 7.90 (1H, s), 7.85 (1H, d, J=8.0 Hz), 7.31 (4H, s), 7.04 (1H, d, J=8.0 Hz), 4.83 (1H, m), 3.77 (2H, m), 3.37 (1H, m), 2.96 (1H, m), 3.08-3.00 (1H, m), 2.91-2.84 (1H, m), 2.41-2.31 (1H, m), 2.24-2.19 (1H, m), 1.78 (2H, m), 1.61 (2H, m), 1.18-0.95 (4H, m), 0.85 (9H, s). Enantiomer B: HPLC/MS and 1H NMR (DMSO-d6) are identical to those of enantiomer A.

Sources & evidence

ORD record: ord-7c3d2a327e714db99ccb3bfadfea08a3
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07803951B2

Reaction notes

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