Acetic Acid → HCID 10076548, compound

HRID 1794922Notes

Reaction equation

HRID 1794922 reaction equation
[CH2:1]([N:5]([C:34](=[O:41])[CH2:35][C:36]([O:38]CC)=[O:37])[C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][CH:15]([NH:18][CH2:19][C@H:20]([OH:33])[C:21]3[CH:26]=[CH:25][C:24]([OH:27])=[C:23]([NH:28][S:29]([CH3:32])(=[O:31])=[O:30])[CH:22]=3)[CH2:14][CH2:13]2)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].[OH-].[Na+].C(O)(=O)C>O.C(O)C>[CH2:1]([N:5]([C:34](=[O:41])[CH2:35][C:36]([OH:38])=[O:37])[C:6]1[CH:7]=[CH:8][C:9]([N:12]2[CH2:17][CH2:16][CH:15]([NH:18][CH2:19][C@H:20]([OH:33])[C:21]3[CH:26]=[CH:25][C:24]([OH:27])=[C:23]([NH:28][S:29]([CH3:32])(=[O:31])=[O:30])[CH:22]=3)[CH2:14][CH2:13]2)=[CH:10][CH:11]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 10698657HCID 10698657, compound

Product 1

HCID 10076548HCID 10076548, compoundYield 19%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of ethyl 3-(butyl-4-(4-[((2R)-2-hydroxy-2-{4-hydroxy-3-l}ethyl)amino]-1-piperidinyl}anilino)-3-oxopropanoate (which was obtained in Example 373)(0.23 g, 0.39 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 hour. The mixture was acidified (pH 6) with glacial acetic acid, concentrated, triturated with water, ethyl acetate, ether, and dried under vacuum to give the titled compound as a tan solid (0.04 g, 19%); 1H NMR (300 MHz, DMSO-d6) δ 1.20–1.50(m, 6 H), 1.70–1.95 (m, 2 H), 2.60–2.80 (m, 5 H), 2.83 (s, 2 H), 2.91(s, 3 H), 3.45–3.70 (m, 4 H), 4.55–4.65(m, 1 H), 6.81(d, J=8.0 Hz, 1 H), 6.90(d, J=8.7 Hz, 2 H), 7.09 (d, J=8.7 Hz, 2 H), 7.07(s, 1 H); MS (ES) m/z: 563.2(MH+); HRMS Calcd. for C27H39N4O7S(MH+): 563.2461. Found: 563.2526.

Workup

  1. concentrationconcentrated
  2. customtriturated with water, ethyl acetate, ether
  3. customdried under vacuum

Sources & evidence

ORD record
ord-f0e0256223e140b8822900ab0977f1d1
Source dataset
uspto-grants-2006_04
Patent number
US07022716B2

Reaction notes

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