Lithium Hydroxide → HCID 178439101, compound

HRID 1717703Notes

Reaction equation

HRID 1717703 reaction equation
[C:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([N:11]([C:28](=[O:39])[CH2:29][C:30]2[CH:35]=[CH:34][C:33]([CH:36]([CH3:38])[CH3:37])=[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-].[NH2:42][C:43]1[NH:47][N:46]=[N:45][N:44]=1>>[C:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([N:11]([C:28](=[O:39])[CH2:29][C:30]2[CH:35]=[CH:34][C:33]([CH:36]([CH3:38])[CH3:37])=[CH:32][CH:31]=2)[CH:12]2[C:20]3[C:15](=[CH:16][C:17]([C:21]([NH:42][C:43]4[NH:47][N:46]=[N:45][N:44]=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 178450645HCID 178450645, compoundHCID 178509299HCID 178509299, compound

Product 1

HCID 178439101HCID 178439101, compound

Procedure

Enantiomer A of butyl 1-{(trans-4-tert-butylcyclohexyl)[(4-isopropylphenyl)acetyl]amino}indane-5-carboxylate (36 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-isopropylphenyl)acetyl]amino}-N-1H-tetrazol-5-ylindane-5-carboxamide. HPLC/MS: m/z=543.5 (M+1), Rt=2.67 min. 1H NMR (DMSO-d6): δ 12.30 (1H, br s), 7.90 (1H, s), 7.85 (1H, d, J=8.0 Hz), 7.17 (2H, d, J=8.0 Hz), 7.10 (2H, d, J=8.0 Hz), 7.03 (1H, d, J=8.0 Hz), 4.79 (1H, m), 3.74 (2H, m), 3.06 (1H, m), 2.88 (1H, m), 2.36 (1H, m), 2.21 (1H, m), 1.74 (2H, m), 1.54 (2H, m), 1.36-0.86 (13H, m), 0.84 (9H, s).

Sources & evidence

ORD record
ord-1bfbcebc0ee5474a9fbf0280f15a494b
Source dataset
uspto-grants-2010_09
Patent number
US07803951B2

Reaction notes

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