Methanol → 5-(2-{tert-Butoxycarbonyl-[2-(3-chloro-phenyl)-2-hydroxy-ethyl]-amino}-propyl)-benzo[1,3]dioxole-2,2-dicarboxylic acid

HRID 1416740Notes

Reaction equation

HRID 1416740 reaction equation
C([O:3][C:4]([C:6]1([C:36]([O:38]CC)=[O:37])[O:10][C:9]2[CH:11]=[CH:12][C:13]([CH2:15][CH:16]([N:18]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:19][CH:20]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=3)[OH:21])[CH3:17])=[CH:14][C:8]=2[O:7]1)=[O:5])C.CO.[OH-].[Na+]>O>[C:32]([O:31][C:29]([N:18]([CH2:19][CH:20]([C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=1)[OH:21])[CH:16]([CH3:17])[CH2:15][C:13]1[CH:12]=[CH:11][C:9]2[O:10][C:6]([C:36]([OH:38])=[O:37])([C:4]([OH:5])=[O:3])[O:7][C:8]=2[CH:14]=1)=[O:30])([CH3:33])([CH3:34])[CH3:35]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 540871285-(2-{tert-Butoxycarbonyl-[2-(3-chloro-phenyl)-2-hydroxy-ethyl]-amino}-propyl)-benzo[1,3]dioxole-2,2-dicarboxylic acid bis-ethyl ester

Product 1

HCID 538189185-(2-{tert-Butoxycarbonyl-[2-(3-chloro-phenyl)-2-hydroxy-ethyl]-amino}-propyl)-benzo[1,3]dioxole-2,2-dicarboxylic acidYield 99.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 5-(2-{tert-butoxycarbonyl-[2-(3-chloro-phenyl)-2-hydroxy-ethyl]-amino}-propyl)-benzo[1,3]dioxole-2,2-dicarboxylic acid bis-ethyl ester (4.42 g, 7.65 mmol), MeOH (100 mL) and H2O (25 mL) was added 5 N NaOH (7.64 mL, 38.2 mmol). After 19 h, the solution was concentrated to an aqueous mixture and acidified to pH=1 with 1 N aq. HCl which turns the solution milky-white. Extraction with 3×100 mL EtOAc, washing the combined organics with 1×200 mL brine, drying over Na2SO4, filtration and concentration gave 3.96 g (99%) of product as a white solid; 1H NMR (300 MHz, DMSO-d6): δ 1.16 (d, J=6.7 Hz, 3H), 1.31 (s, 9H), 2.55-2.70 (m, 1H), 2.80-2.92 (m, 1H), 3.05-3.23 (m, 2H), 3.71-3.93 (m, 2H), 4.62-4.87 (m, 2H), 5.30-5.90 (brs, 1H), 6.59-6.99 (complexm, 4H), 7.14-7.47 (complexm, 3H), 8.60-8.80 (brs, 1H); MS (ES) m/z (relative intensity): 522. (M+ +H, 50).

Workup

  1. concentrationthe solution was concentrated to an aqueous mixture
  2. extractionExtraction with 3×100 mL EtOAc
  3. washwashing the combined organics with 1×200 mL brine
  4. dry with materialdrying over Na2SO4, filtration and concentration

Sources & evidence

ORD record
ord-054b9eab423c4134a142a3a1741ae19b
Source dataset
uspto-grants-1999_06
Patent number
US05914339

Reaction notes

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