Hydrochloric Acid → HCID 57670776, compound

HRID 545626Notes

Reaction equation

HRID 545626 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-8c06f053842a46149eba0364fa0319c1
Source dataset
uspto-grants-2011_05
Patent number
US07935725B2

Reaction notes

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