Sodium Hydroxide → HCID 53716194, compound

HRID 2298641Notes

Reaction equation

HRID 2298641 reaction equation
[C:1]([O:5][C:6]([NH:8][N:9]=[CH:10][C:11]1[S:15][C:14]([CH3:16])=[C:13]([C:17]2[S:18][CH:19]=[C:20]([C:22]3[CH:23]=[C:24]([CH:31]=[CH:32][CH:33]=3)[O:25][CH2:26][C:27]([O:29]C)=[O:28])[N:21]=2)[CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>O1CCCC1>[C:1]([O:5][C:6]([NH:8][N:9]=[CH:10][C:11]1[S:15][C:14]([CH3:16])=[C:13]([C:17]2[S:18][CH:19]=[C:20]([C:22]3[CH:23]=[C:24]([CH:31]=[CH:32][CH:33]=3)[O:25][CH2:26][C:27]([OH:29])=[O:28])[N:21]=2)[CH:12]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69938167HCID 69938167, compound

Product 1

HCID 53716194HCID 53716194, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 50 mg (0.11 mmol) of methyl 2-{3-[2-(5-{[(tert-butoxy)carbonylamino]iminomethyl}-2-methyl-3-thienyl)-1,3-thiazol-4-yl]phenoxy}acetate was dissolved in tetrahydrofuran (10 mL) and treated 2M aqueous sodium hydroxide solution (2 mL) at room temperature for 1 h 10 min. The solvents were removed in vacuo. Purification by passing the solid through silica gel (1 inch in a 60 mL scintered-glass Büchner funnel) eluting with dichloromethane:methanol 8/2 (v:v) gave 2-{3-[2-(5-{[(tert-butoxy)carbonylamino]iminomethyl}-2-methyl-3-thienyl)-1,3-thiazol-4-yl]phenoxy}acetic acid (44 mg, 88%) as a yellow solid. 1H-NMR (DMSO-d6; 300 MHz) δ9.38 (br s, 2H), 8.94 (br s, 2H), 8.51 (s, 1H), 8.31 (s, 1H), 7.62 (m, 2H), 7.41 (m, 1H), 6.96 (m, 1H), 4.89 (s, 2H), 3.72 (s, 3H), 2.92 (s, 3H). Mass spectrum (ESI, m/z): Calcd. for C22H23N3O5S2 474.1 (M+H), 374.1 ((M-BOC)+H) found 374.2, 473.7.

Workup

  1. customThe solvents were removed in vacuo
  2. customPurification
  3. washeluting with dichloromethane

Sources & evidence

ORD record
ord-71f9f76985b64b3288a75674753c83fa
Source dataset
uspto-grants-2002_12
Patent number
US06492403B1

Reaction notes

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