DL-cysteine → 2-(7-(4-Cyclopentyl-3-(trifluoromethyl)benzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic Acid

HRID 515669Notes

Reaction equation

HRID 515669 reaction equation
[CH:1]1([C:6]2[CH:33]=[CH:32][C:9]([CH2:10][O:11][C:12]3[CH:20]=[CH:19][C:18]4[N:17]5[CH2:21][CH2:22][CH:23]([CH2:24][C:25]([O:27]C(C)(C)C)=[O:26])[C:16]5=[CH:15][C:14]=4[CH:13]=3)=[CH:8][C:7]=2[C:34]([F:37])([F:36])[F:35])[CH2:5][CH2:4][CH2:3][CH2:2]1.NC(CS)C(O)=O>C(O)(C(F)(F)F)=O>[CH:1]1([C:6]2[CH:33]=[CH:32][C:9]([CH2:10][O:11][C:12]3[CH:20]=[CH:19][C:18]4[N:17]5[CH2:21][CH2:22][CH:23]([CH2:24][C:25]([OH:27])=[O:26])[C:16]5=[CH:15][C:14]=4[CH:13]=3)=[CH:8][C:7]=2[C:34]([F:37])([F:35])[F:36])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 594DL-cysteineHCID 67248866tert-Butyl 2-(7-(4-Cyclopentyl-3-(trifluoromethyl)benzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate

Product 1

HCID 461749052-(7-(4-Cyclopentyl-3-(trifluoromethyl)benzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic AcidYield 83.5%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
23 °C

Procedure

tert-Butyl 2-(7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate (0.800 g, 1.558 mmol) was added to a solution of 2-amino-3-mercaptopropanoic acid (0.189 g, 1.558 mmol) in TFA (10 mL). The reaction mixture was stirred at 23° C. for 15 min in a 20 mL sealed scintillation vial. After 15 min the reaction mixture was poured into ice water and a precipitate formed. The precipitate was collected by filtration, washed with hexanes (3×20 mL) and dried (vacuum oven) to provide the title compound as a white solid (0.595 g). LCMS m/z=458.4 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 1.53-1.74 (m, 4H), 1.79-1.89 (m, 2H), 1.94-2.04 (m, 2H), 2.15-2.26 (m, 1H), 2.51-2.69 (m, 2H), 2.72-2.83 (m, 1H), 3.23-3.27 (m, 1H), 3.58 (quintet, J=7.20 Hz, 1H), 3.91-4.00 (m, 1H), 4.05-4.14 (m, 1H), 5.13 (s, 2H), 6.01 (s, 1H), 6.77 (dd, J=8.72, 2.40 Hz, 1H), 7.07 (d, J=2.27 Hz, 1H), 7.19 (d, J=8.84 Hz, 1H), 7.62 (d, J=8.08 Hz, 1H), 7.68-7.71 (m, 2H), 12.27 (s, 1H).

Workup

  1. customsealed scintillation vial
  2. customa precipitate formed
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with hexanes (3×20 mL)
  5. customdried (vacuum oven)

Sources & evidence

ORD record
ord-09db29301c6d4ecfb8d0430403c004bd
Source dataset
uspto-grants-2015_08
Patent number
US09108969B2

Reaction notes

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