Hydrochloric Acid → HCID 57670776, compound

HRID 1799086Notes

Reaction equation

HRID 1799086 reaction equation
C[O:2][C:3](=[O:36])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]2[CH2:18][CH:17]3[CH:13]([CH2:14][N:15]([CH2:19][C:20]4[CH:25]=[CH:24][C:23]([O:26][C:27]5[S:28][C:29]6[CH:35]=[CH:34][CH:33]=[CH:32][C:30]=6[N:31]=5)=[CH:22][CH:21]=4)[CH2:16]3)[CH2:12]2)=[CH:6][CH:5]=1.O.[OH-].[K+].Cl>C(O)(C)C.C(Cl)Cl>[S:28]1[C:29]2[CH:35]=[CH:34][CH:33]=[CH:32][C:30]=2[N:31]=[C:27]1[O:26][C:23]1[CH:22]=[CH:21][C:20]([CH2:19][N:15]2[CH2:14][CH:13]3[CH2:12][N:11]([CH2:10][C:7]4[CH:6]=[CH:5][C:4]([C:3]([OH:36])=[O:2])=[CH:9][CH:8]=4)[CH2:18][CH:17]3[CH2:16]2)=[CH:25][CH:24]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 57670737HCID 57670737, compound

Product 1

HCID 57670776HCID 57670776, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-{5-[4-(benzothiazol-2-yloxy)-benzyl]-hexahydro-pyrrolo[3,4-c]pyrrol-2-ylmethyl)-benzoic acid methyl ester (58.5 mg, 0.12 mmol, 1 equiv) in isopropanol (2.5 mL) was added water (1.1 mL) followed by the addition of aq. KOH (13 mg in 2.5 mL water). The reaction stirred at rt for 16 h. The reaction mixture was acidified to pH 6 with 6 N HCl, and CH2Cl2 was added. The layers were separated and the aqueous layer was extracted with 25% isopropanol/CH2Cl2 (2×10 mL). The combined organics were dried, filtered and concentrated to afford the title compound (32 mg, 56%). MS (ESI): mass calcd. for C28H27N3O3S, 485.61; m/z found, 486.2 [M+H]+. 1H NMR (500 MHz, CDCl3): 8.01 (d, J=8.2 Hz, 2H), 7.71 (m, 2H), 7.52-7.44 (m, 4H), 7.43-7.34 (m, 4H), 3.95 (m, 4H), 3.13 (s, 3H), 2.81 (m, 5H), 2.03 (s, 1H), 1.27 (s, 2H).

Workup

  1. additionwas added
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with 25% isopropanol/CH2Cl2 (2×10 mL)
  4. customThe combined organics were dried
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f44b3584bdc349b898e7c0216bf3482a
Source dataset
uspto-grants-2013_01
Patent number
US08344008B2

Reaction notes

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