DL-cysteine → HCID 58329597, compound

HRID 1964134Notes

Reaction equation

HRID 1964134 reaction equation
[CH:1]1([C:6]2[CH:35]=[CH:34][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]([CH2:32][CH3:33])[C:14]=4[CH:13]=3)=[CH:8][C:7]=2[C:36]([F:39])([F:38])[F:37])[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:35]=[CH:34][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]([CH2:32][CH3:33])[C:14]=4[CH:13]=3)=[CH:8][C:7]=2[C:36]([F:39])([F:37])[F:38])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 594DL-cysteineHCID 86654872HCID 86654872, compound

Product 1

HCID 58329597HCID 58329597, compoundYield 13.7%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
23 °C

Procedure

tert-Butyl 2-(7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-9-ethyl-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate (6.6 mg, 0.012 mmol) was added to a solution of 2-amino-3-mercaptopropanoic acid (1.476 mg, 0.012 mmol) in TFA (1 mL). The reaction was stirred at 23° C. for 15 min in a 20 mL sealed scintillation vial. The mixture was poured into about 4 mL of ice water. The precipitate was collected by vacuum filtration through a glass fiber paper, washed with n-hexane (3×5 mL), and dried (vacuum oven) to give the title compound (0.8 mg) as a tan solid. LCMS m/z=486.3 [M+H]+; 1H NMR (400 MHz, CD3CN) δ ppm 1.09 (t, J=7.52 Hz, 3H), 1.48-1.59 (m, 2H), 1.60-1.69 (m, 2H), 1.74-1.82 (m, 2H), 1.93-2.00 (m, 2H), 2.17-2.27 (m, 1H), 2.39-2.49 (m, 1H), 2.55-2.63 (m, 2H), 2.66-2.81 (m, 2H), 3.21-3.32 (m, 1H), 3.54-3.63 (m, 1H), 3.82-3.89 (m, 1H), 3.92-4.00 (m, 1H), 5.05 (s, 2H), 6.70 (dd, J=8.72, 2.40 Hz, 1H), 6.96 (d, J=2.27 Hz, 1H), 7.03 (d, J=8.72 Hz, 1H), 7.49 (d, 1H), 7.57 (d, J=9.35 Hz, 1H), 7.64 (d, J=1.14 Hz, 1H), 8.95 (bs, 1H).

Workup

  1. customsealed scintillation vial
  2. filtrationThe precipitate was collected by vacuum filtration through a glass fiber paper
  3. washwashed with n-hexane (3×5 mL)
  4. customdried (vacuum oven)

Sources & evidence

ORD record
ord-9025e38b130b4d5c92100bc82e3831dd
Source dataset
uspto-grants-2013_04
Patent number
US08415484B2

Reaction notes

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