Lithium hydroxide, monohydrate → HCID 9872055, compound

HRID 1356207Notes

Reaction equation

HRID 1356207 reaction equation
C[O:2][C:3](=[O:40])[C:4]1[CH:9]=[C:8]([CH2:10][C@H:11]([NH:24][S:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)(=[O:27])=[O:26])[C:12](=[O:23])[NH:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[CH:7]=[CH:6][C:5]=1[O:34][CH2:35][C:36]([O:38]C)=[O:37].O.[OH-].[Li+]>C1COCC1.O>[C:28]1([S:25]([NH:24][C@H:11]([C:12](=[O:23])[NH:13][CH2:14][C:15]2[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=2)[CH2:10][C:8]2[CH:7]=[CH:6][C:5]([O:34][CH2:35][C:36]([OH:38])=[O:37])=[C:4]([CH:9]=2)[C:3]([OH:40])=[O:2])(=[O:27])=[O:26])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 12069136HCID 12069136, compound

Product 1

HCID 9872055HCID 9872055, compound

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

5-[(2S)-2-Benzenesulfonylamino-2-(4-methoxy-benzylcarbamoyl)-ethyl]-2-methoxycarbonylmethoxy-benzoic acid methyl ester Step H (17 mg, 0.30 mmol) is stirred in 3:2 THF/H2O (3 mL) at RT. Lithium hydroxide monohydrate (20 mg, 0.5 mmol) is added and the reaction is stirred overnight. The mixture is partitioned between EtOAc (15 mL) and 2N HCl (15 mL). The organics are washed with saturated NaCl (1×15 mL), filtered and concentrated to afford the title compound (compound 1), 5-[(2S)-2-benzenesulfonylamino-2-(4-methoxy-benzylcarbamoyl)-ethyl]-2-carboxymethoxy-benzoic acid; 1H NMR (400 MHz, CDCl3) δ7.65 (d, 2H), 7.51 (m, 1H), 7.38 (m, 3H), 7.20 (d, 1H), 7.01 (d, 2H), 6.80 (d, 2H), 6.68 (d, 1H), 4.73 (s, 2H), 4.17 (m, 2H), 3.94 (m, 1H), 3.78 (s, 3H), 2.99 (dd, 1H), 2.91 (dd, 1H); MS (ES−) m/z 541 (M−1).

Workup

  1. customThe mixture is partitioned between EtOAc (15 mL) and 2N HCl (15 mL)
  2. washThe organics are washed with saturated NaCl (1×15 mL)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d81928f7ca4f4d3497d764354e35542c
Source dataset
uspto-grants-2003_07
Patent number
US06586467B2

Reaction notes

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