DL-cysteine → 2-(7-(4-Cyclopentyl-3-(trifluoromethyl)benzyloxy)-9-methyl-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic Acid

HRID 1964099Notes

Reaction equation

HRID 1964099 reaction equation
[CH:1]1([C:6]2[CH:34]=[CH:33][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=[C:15]([CH3:32])[C:14]=4[CH:13]=3)=[CH:8][C:7]=2[C:35]([F:38])([F:37])[F:36])[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:34]=[CH:33][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=[C:15]([CH3:32])[C:14]=4[CH:13]=3)=[CH:8][C:7]=2[C:35]([F:38])([F:36])[F:37])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 594DL-cysteineHCID 67376009tert-Butyl 2-(7-(4-Cyclopentyl-3-(trifluoromethyl)benzyloxy)-9-methyl-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate

Product 1

HCID 583295742-(7-(4-Cyclopentyl-3-(trifluoromethyl)benzyloxy)-9-methyl-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)-9-methyl-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate (17.5 mg, 0.033 mmol) was added to a solution of 2-amino-3-mercaptopropanoic acid (4.02 mg, 0.033 mmol) in TFA (1 mL) and were stirred at 23° C. for 15 min in a 20 mL sealed scintillation vial. After 15 min, the reaction mixture was poured into about 4 mL of ice water. A precipitate was formed and collected by vacuum filtration. The solid was washed with n-hexane (3×5 mL) and dried (vacuum oven) to give the title compound as a tan solid (13 mg). LCMS m/z=472.4 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 1.54-1.73 (m, 4H), 1.80-1.90 (m, 2H), 1.95-2.05 (m, 2H), 2.15 (s, 3H), 2.18-2.30 (m, 1H), 2.42-2.48 (m, 1H), 2.69-2.83 (m, 2H), 3.20-3.31 (m, 1H), 3.56-3.66 (m, 1H), 3.87-3.96 (m, 1H), 3.98-4.08 (m, 1H), 5.14 (s, 2H), 6.76 (dd, J=8.72, 2.40 Hz, 1H), 7.02 (d, J=2.27 Hz, 1H), 7.14 (d, J=8.72 Hz, 1H), 7.63 (d, J=7.96 Hz, 1H), 7.68-7.77 (m, 2H), 12.33 (bs, 1H).

Workup

  1. customsealed scintillation vial
  2. waitAfter 15 min
  3. customA precipitate was formed
  4. filtrationcollected by vacuum filtration
  5. washThe solid was washed with n-hexane (3×5 mL)
  6. customdried (vacuum oven)

Sources & evidence

ORD record
ord-6fb0bd67e2d74e5e9926beb61666b588
Source dataset
uspto-grants-2013_04
Patent number
US08415484B2

Reaction notes

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