Acetic Acid → HCID 10145298, compound

HRID 1278767Notes

Reaction equation

HRID 1278767 reaction equation
C([O:3][C:4](=[O:42])[CH2:5][N:6]([CH2:38][CH:39]1[CH2:41][CH2:40]1)[S:7]([C:10]1[CH:15]=[CH:14][C:13]([N:16]2[CH2:21][CH2:20][CH:19]([NH:22][CH2:23][C@H:24]([OH:37])[C:25]3[CH:30]=[CH:29][C:28]([OH:31])=[C:27]([NH:32][S:33]([CH3:36])(=[O:35])=[O:34])[CH:26]=3)[CH2:18][CH2:17]2)=[CH:12][CH:11]=1)(=[O:9])=[O:8])C.O.[OH-].[Li+].C(O)(=O)C>C(O)C.O>[CH:39]1([CH2:38][N:6]([CH2:5][C:4]([OH:42])=[O:3])[S:7]([C:10]2[CH:15]=[CH:14][C:13]([N:16]3[CH2:17][CH2:18][CH:19]([NH:22][CH2:23][C@H:24]([OH:37])[C:25]4[CH:30]=[CH:29][C:28]([OH:31])=[C:27]([NH:32][S:33]([CH3:36])(=[O:34])=[O:35])[CH:26]=4)[CH2:20][CH2:21]3)=[CH:12][CH:11]=2)(=[O:9])=[O:8])[CH2:41][CH2:40]1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 168937Lithium hydroxide, monohydrateHCID 10189352HCID 10189352, compound

Product 1

HCID 10145298HCID 10145298, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of 0.15 9 (0.24 mmol) of [cyclopropylmethyl-(4-{4-[(2R)-2-hydroxy-2-(4-hydroxy-3-methanesulfonylamino-phenyl)-ethylamino]-piperidin-1-yl}-benzenesulfonyl)-amino]-acetic acid ethyl ester ( ) in 2 mL of ethanol, 0.1 g (2.4 mmol) of lithium hydroxide monohydrate in 2 ml of water was added dropwise over 10 minutes. After 20 minutes, the reaction mixture was quenched with .13 ml (2.4 mmol) of glacial acetic acid. The solvent was removed in vacuo and the pink aqueous residue was pipetted out of the flask. The solid was then washed with water and ethyl acetate and then dried via vacuum line to give 0.134 g of the title compound as a tan solid; 1H NMR (DMSO) δ 0.82 (m, 1H), 1.41 (m, 2H), 1.85-1.97 (m, 2H), 2.68-2.82 (m, 8H), 2.92 (s, 3H), 3.04 (d, J=6.84 Hz, 2H), 3.30 (m, 5H), 3.76 (m, 4H), 4.58 (m, 1H), 6.83 (d, J=8.25 Hz, 1H), 6.94-7.05 (m, 3H), 7.18 (d, J=1.86 Hz, 1H), 7.60 (d, J=8.88 Hz, 2H); MS (ES) m/z 597.1 (MH+); HRMS (MH−) for C26H36N4O8S2: 595.1904.

Workup

  1. customThe solvent was removed in vacuo
  2. washThe solid was then washed with water and ethyl acetate
  3. customdried via vacuum line

Sources & evidence

ORD record
ord-8f49a38fccca4266a6c3e6f4fed15f61
Source dataset
uspto-grants-2002_09
Patent number
US06444685B1

Reaction notes

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