Lithium Hydroxide → HCID 178445691, compound

HRID 1717705Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[C:12](OC)=[O:13])[O:8][CH2:7][CH2:6][CH:5]2[N:16]([C@H:31]1[CH2:36][CH2:35][C@H:34]([C:37]([CH3:40])([CH3:39])[CH3:38])[CH2:33][CH2:32]1)[C:17]([NH:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][C:27]([F:30])([F:29])[F:28])=[CH:22][CH:21]=1)=[O:18].[Li+].[OH-].Cl.C[O:45][C:46](=[O:50])[CH2:47][CH2:48][NH2:49]>>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[C:12]([NH:49][CH2:48][CH2:47][C:46]([OH:50])=[O:45])=[O:13])[O:8][CH2:7][CH2:6][CH:5]2[N:16]([C@H:31]1[CH2:36][CH2:35][C@H:34]([C:37]([CH3:38])([CH3:40])[CH3:39])[CH2:33][CH2:32]1)[C:17]([NH:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][C:27]([F:28])([F:30])[F:29])=[CH:22][CH:21]=1)=[O:18]

Participants

Reactant 3

HCID 3939Lithium Hydroxide

HCID 2734767Methyl 3-aminopropanoate hydrochloride

HCID 178496889HCID 178496889, compound

Product 1

HCID 178445691HCID 178445691, compound

Procedure

Enantiomer A of methyl 6-bromo-4-[(trans-4-tert-butylcyclohexyl)({[4-(trifluoromethoxy)phenyl]amino}carbonyl)amino]chromane-7-carboxylate (25 mg) was saponified with aqueous LiOH and then coupled to β-alanine methyl ester HCl salt following the procedure described (Example 3/4) to give N-({6-bromo-4-[(trans-4-tert-butylcyclohexyl)({[4-(trifluoromethoxy)phenyl]amino}carbonyl)amino]-3,4-dihydro-2H-chromen-7-yl}carbonyl)-β-alanine. HPLC/MS: m/z=684.2 (M+1), Rt=2.50 min. 1H NMR (DMSO-d6): δ 12.20 (1H, br s), 8.56 (1H, s), 8.38 (1H, t, J=5.5 Hz), 7.46 (2H, d, J=9.0 Hz), 7.21 (2H, d, J=9.0 Hz), 6.72 (1H, s), 4.68 (1H, m), 4.36 (1H, dt, J=2.0 Hz, 11.5 Hz), 4.20 (1H, t, J=11.5 Hz), 3.90 (1H, m), 3.37 (2H, m), 2.73 (1H, m), 2.48 (2H, t, J=7.0 Hz), 1.98-1.72 (7H, m), 1.28-1.04 (4H, m), 0.88 (9H, s).

Sources & evidence

ORD record: ord-cbe9cd5eda8d4a799dd6a698c5cf568e
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07803951B2

Reaction notes

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