Lithium Hydroxide → HCID 10459917, compound

HRID 2121254Notes

Reaction equation

HRID 2121254 reaction equation
C[O:2][C:3](=[O:40])[C@H:4]([CH2:36][CH2:37][S:38][CH3:39])[NH:5][C:6](=[O:35])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][N:14]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)=[CH:9][C:8]=1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[CH3:34].[OH-].[Li+]>>[CH2:21]([N:14]([CH2:13][C:10]1[CH:11]=[CH:12][C:7]([C:6]([NH:5][C@H:4]([C:3]([OH:40])=[O:2])[CH2:36][CH2:37][S:38][CH3:39])=[O:35])=[C:8]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[CH3:34])[CH:9]=1)[C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

3

Reactant 2

HCID 3939Lithium HydroxideHCID 20622837HCID 20622837, compound

Product 1

HCID 10459917HCID 10459917, compoundYield 100%

Procedure

To a stirred solution of the ester resulting from example 407C (15.51 g, 28 mmol) on methanol (120 mL) at 0° C. was added 1 N aqueous lithium hydroxide (56 mL, 56 mmol, 2 eq). The cooling bath was removed and the mixture was stirred for 2 hours. The solvent was removed in vacuo and the residue diluted with water (400 mL). The solution was carefully acidified to pH 4, and the resultant precipitate collected by filtration to afford the title compound (14.08 g, 100%). 1H NMR (300 MHz, DMSO d6) δ 8.18 (d, 1H), 8.03 (bs, 1H), 7.82 (bs, 1H), 7.48 (d, 1H), 7.30 (m, 6H), 7.19 (m, 2H), 7.10 (m, 4H), 4.84 (s, 2H), 4.79 (s, 2H), 1.96-2.23 (m, 5H), 1.96 (s, 3H), 1.63-1.89 (m, 2H). MS m/e 540 (M+H)+, 522. Anal calcd for C32H33N3O3S (+1.18H2O): C, 68.51; N, 7.31. Found: C, 68.52; H, 6.35; N, 7.49.

Workup

  1. customThe cooling bath was removed
  2. customThe solvent was removed in vacuo
  3. additionthe residue diluted with water (400 mL)
  4. filtrationthe resultant precipitate collected by filtration

Sources & evidence

ORD record
ord-edcdc9964a2a4d669bdc40f75e5e05e5
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

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