Sodium Hydroxide → HCID 1215342, compound

HRID 881580Notes

Reaction equation

HRID 881580 reaction equation
[OH-].[Na+].[C:3]([NH:11][C:12]1[CH:31]=[CH:30][CH:29]=[CH:28][C:13]=1[C:14]([NH:16][C:17]1[CH:27]=[CH:26][CH:25]=[CH:24][C:18]=1[C:19]([O:21]CC)=[O:20])=[O:15])(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>N1C=CC=CC=1.C(Cl)Cl>[C:3]([NH:11][C:12]1[CH:31]=[CH:30][CH:29]=[CH:28][C:13]=1[C:14]([NH:16][C:17]1[CH:27]=[CH:26][CH:25]=[CH:24][C:18]=1[C:19]([OH:21])=[O:20])=[O:15])(=[O:10])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 57387790HCID 57387790, compound

Product 1

HCID 1215342HCID 1215342, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

NaOH (aq, 2 M, 0.7 mL) was added to a stirred solution of ester 23a (53.1 mg, 0.14 mmol) in pyridine (0.7 mL) at room temperature. After 3 h, the reaction was diluted with DCM and washed with HCl (3×, 1 M in brine), NaHCO3 (aq, sat), brine and dried over Na2SO4 before being purified by preparative HPLC to give acid 23b in 70% yield (35 mg).

Workup

  1. washwashed with HCl (3×, 1 M in brine), NaHCO3 (aq, sat), brine
  2. dry with materialdried over Na2SO4
  3. custombefore being purified by preparative HPLC

Sources & evidence

ORD record
ord-1b48819017054e179812ffe2f3d9a685
Source dataset
uspto-grants-2015_03
Patent number
US08993622B2

Reaction notes

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