Sodium Hydroxide → HCID 67243532, compound

HRID 2422935Notes

Reaction equation

HRID 2422935 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:24][NH:25][S:26]([C:29]2[CH:34]=[CH:33][C:32](C)=[CH:31][CH:30]=2)(=[O:28])=[O:27])[CH2:9][C:10]([NH:12][C:13]2[CH:23]=[CH:22][C:16]([C:17]([O:19]CC)=[O:18])=[CH:15][CH:14]=2)=[O:11])=[CH:4][CH:3]=1.[OH-:36].[Na+]>CO.C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:24][NH:25][S:26]([C:29]2[CH:34]=[CH:33][C:32]([O:36][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:31][CH:30]=2)(=[O:28])=[O:27])[CH2:9][C:10]([NH:12][C:13]2[CH:23]=[CH:22][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=2)=[O:11])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 24785949HCID 24785949, compound

Product 1

HCID 67243532HCID 67243532, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of ester 38 (0.065 g, 0.107 mmol) in methanol (1.5 ml) and THF (1.5 ml) was stirred in presence of NaOH 1M (1 ml) for 2 h at 80° C. After cooling to rt, the solution remaining was concentrated in vacuo. HCl 1M (1.5 ml) was added and the formed white solid was filtered, washed with water (10 ml) and dried. The pure acid 40 was obtained without further need for purification (0.050 g, 0.088 mmol, 83%), mp 119-121° C. 1H NMR (400 MHz, CD3OD) δ 2.61 (1H, dd, J 8.4, 14.8 Hz, H—CHCO), 2.82 (1H, dd, J 6.0, 14.8 Hz, H—CHCO), 3.09 (1H, dd, J 7.8, 13.4 Hz, H—CHNH), 3.16 (1H, dd, J 6.4, 13.2 Hz, H—CHNH), 6.99 (2H, d, J 9.2 Hz), 7.06-7.08 (2H, m), 7.17-7.24 (5H, m), 7.47.44 (2H, m), 7.54 (2H, d, J 9.2 Hz), 7.72 (2H, d, J 8.8 Hz), 7.91 (2H, d, J 9.2 Hz). 13C NMR (400 MHz, CD3OD) δ. νmax (pure sample)/(cm−1) 3359 (st) (OH), 1686 (st) (C═O), 1595 (st) (C═O), 1530 (st), 1487 (st), 1410 (md), 1318 (md), 1246 (st), 1150 (st) 1092 (md). MS (API-ES): m/z 563 [M+H]+ (100%), HRMS (API-ES) m/z found 563.10436 [M−H]−.

Workup

  1. concentrationthe solution remaining was concentrated in vacuo
  2. additionHCl 1M (1.5 ml) was added
  3. filtrationthe formed white solid was filtered
  4. washwashed with water (10 ml)
  5. customdried

Sources & evidence

ORD record
ord-06663cb86afb4d3fab97f542b7f20778
Source dataset
uspto-grants-2011_06
Patent number
US07960434B2

Reaction notes

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