Acetic Acid → HCID 10553603, compound

HRID 1794921Notes

Reaction equation

HRID 1794921 reaction equation
[OH:1][C@H:2]([C:26]1[CH:31]=[CH:30][C:29]([OH:32])=[C:28]([NH:33][S:34]([CH3:37])(=[O:36])=[O:35])[CH:27]=1)[CH2:3][NH:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:25]=[CH:24][C:14]([NH:15][C:16](=[O:23])[CH2:17][C:18]([O:20]CC)=[O:19])=[CH:13][CH:12]=2)[CH2:7][CH2:6]1.[OH-].[Na+].C(O)(=O)C>O.C(O)C>[OH:1][C@H:2]([C:26]1[CH:31]=[CH:30][C:29]([OH:32])=[C:28]([NH:33][S:34]([CH3:37])(=[O:35])=[O:36])[CH:27]=1)[CH2:3][NH:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:12]=[CH:13][C:14]([NH:15][C:16](=[O:23])[CH2:17][C:18]([OH:20])=[O:19])=[CH:24][CH:25]=2)[CH2:7][CH2:6]1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 10649991HCID 10649991, compound

Product 1

HCID 10553603HCID 10553603, compoundYield 59.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of ethyl 3-(4-{4-[((2R)-2-hydroxy-2-{4-hydroxy-3-[(methylsulfonyl)amino]phenyl}ethyl)amino]-1-piperidinyl}anilino)-3-oxopropanoate (which was obtained in Example 371)(0.23 g, 0.43 mmol) in distilled water (3 mL) and ethanol (2 mL) was added 1 N sodium hydroxide (2 mL). The reaction was stirred at room temperature for 1 hr. The reaction mixture was made acidic (pH 6) with glacial acetic acid, concentrated, triturated with water, ether, ethyl acetate to give the title compound as a light yellow solid (0.13 g, 59%); 1H NMR (300 MHz, DMSO-d6) δ 1.30–1.45(m, 2 H), 1.80–1.95 (m, 2 H), 2.50–2.80 (m, 5 H), 2.90 (s, 2 H), 2.91(s, 3 H), 3.45–3.60 (m, 2 H), 4.48–4.53(m, 1 H), 6.80–6.90(m, 3H), 7.00(d, J=8.3 Hz, 1 H), 7.18 (d, J=1.6 Hz, 1 H), 7.38(d, J=9.0 Hz, 2 H), 11.50–11.60(m, 1 H); MS (ES) m/z: 505.3 (M−H)−; HRMS Calcd. for C23H31N4O7S (MH+): 507.1908. Found: 507.1895.

Workup

  1. concentrationconcentrated
  2. customtriturated with water, ether, ethyl acetate

Sources & evidence

ORD record
ord-f30ba200326a4dd18d67a95e77b718d2
Source dataset
uspto-grants-2006_04
Patent number
US07022716B2

Reaction notes

Loading…