Potassium Hydroxide → HCID 42598147, compound

HRID 1799087Notes

Reaction equation

HRID 1799087 reaction equation
C[O:2][C:3](=[O:30])[CH2:4][N:5]1[CH2:12][CH:11]2[CH:7]([CH2:8][N:9]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([O:20][C:21]4[S:22][C:23]5[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=5[N:25]=4)=[CH:16][CH:15]=3)[CH2:10]2)[CH2:6]1.[OH-].[K+]>C(O)(C)C.O>[S:22]1[C:23]2[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=2[N:25]=[C:21]1[O:20][C:17]1[CH:16]=[CH:15][C:14]([CH2:13][N:9]2[CH2:8][CH:7]3[CH2:6][N:5]([CH2:4][C:3]([OH:30])=[O:2])[CH2:12][CH:11]3[CH2:10]2)=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 57670736HCID 57670736, compound

Product 1

HCID 42598147HCID 42598147, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 21889133Propan-2-ol--water (1/1)Solvent

Procedure

A solution of {5-[4-(benzothiazol-2-yloxy)-benzyl]-hexahydro-pyrrolo[3,4-c]pyrrol-2-yl}-acetic acid methyl ester (233 mg, 0.55 mmol) in 1:1 isopropanol/water (2 mL) was treated with KOH (62 mg, 1.1 mmol). The reaction stirred at rt overnight. The reaction was acidified to pH 6.5 and extracted with 25% isopropanol/CHCl3 to afford pure acid as a white powder (67 mg, 30%). MS (ESI): Mass calcd for C22H23N3O3S, 409.5; m/z found, 410.2 [M+H]+; 1H NMR (400 MHz, CD3OD): 7.78 (d, J=8.0 Hz, 1H), 7.65 (d, J=8.1 Hz, 1H), 7.57 (d, J=8.6 Hz, 2H), 7.45-7.35 (m, 3H), 7.34-7.28 (m, 1H), 3.76 (s, 2H), 3.64 (s, 2H), 3.55-3.35 (m, 4H), 3.12-2.97 (m, 2H), 2.94 (d, J=9.9 Hz, 2H), 2.52-2.34 (m, 2H).

Workup

  1. extractionextracted with 25% isopropanol/CHCl3

Sources & evidence

ORD record
ord-57ebfbaa094d4c0f9f7472ac35f02173
Source dataset
uspto-grants-2013_01
Patent number
US08344008B2

Reaction notes

Loading…