Lithium Hydroxide → HCID 23299460, compound

HRID 1457713Notes

Reaction equation

HRID 1457713 reaction equation
[CH2:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH2:26][CH:25]([N:27]([S:34]([CH2:37][CH2:38][CH2:39][CH3:40])(=[O:36])=[O:35])[CH2:28][CH2:29][C:30]([O:32]C)=[O:31])[O:24][N:23]=3)=[CH:18][CH:17]=2)[CH2:10][CH2:9]1)=[O:7])[CH2:2][CH2:3][CH3:4].[Li+].[OH-]>C1COCC1>[CH2:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH2:26][CH:25]([N:27]([S:34]([CH2:37][CH2:38][CH2:39][CH3:40])(=[O:36])=[O:35])[CH2:28][CH2:29][C:30]([OH:32])=[O:31])[O:24][N:23]=3)=[CH:18][CH:17]=2)[CH2:10][CH2:9]1)=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 23299510HCID 23299510, compound

Product 1

HCID 23299460HCID 23299460, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 3-(3-[4-{(butyloxycarbonylpiperidin-4-yl)methoxy)phenyl]isoxazolin-5-yl{[butanesulfonyl]amino})propionate more polar diastereomer (200 mg, 0.344 mmol) in THF (1 mL) was saponified using 0.5M LiOH (1 mL, 0.5 mmol) over 4 hours as per Example 1, Part F. The crude carboxylic acid was crystallized from EtOAc/hexanes, affording 77 mg (39%) of the desired material; mp: 137.3°-139.0° C.; 1H NMR (300 MHz, CDCl3) δ 7.55 (d, J=8.8 Hz, 2H), 6.87 (d, J=8.8 Hz, 2H), 5.45 (d, J=9.5 Hz, 1H), 4.92 (m, 1H), 4.37 (m, 1H), 4.15 (b, 2H), 3.81, (d, J=6.2 Hz, 2H), 3.47 (dd, J=16.5, 9.9 Hz, 1H), 3.08 (t, J=8.1 Hz, 2H), 3.01 (dd, J=16.5, 7.0 Hz, 1H), 2.74 (bt, J=12.1 Hz, 2H), 2.26 (m, 1H), 2.01 (m, 2H), 1.81 (m, 4H), 1.45 (s, 9H, overlapped with m, 1H), 1.24 (m, 3H), 0.91 (t, J=7.3 Hz, 3H).

Workup

  1. customover 4 hours
  2. customThe crude carboxylic acid was crystallized from EtOAc/hexanes

Sources & evidence

ORD record
ord-01a451aa762d4b8cb5f4732d026a5fc9
Source dataset
uspto-grants-1998_12
Patent number
US05849736

Reaction notes

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