DL-cysteine → HCID 58329578, compound

HRID 1964108Notes

Reaction equation

HRID 1964108 reaction equation
NC(CS)C(O)=O.C(O)(C(F)(F)F)=O.[CH2:15]([C:19]1[CH:46]=[CH:45][C:22]([CH2:23][O:24][C:25]2[CH:33]=[CH:32][C:31]3[N:30]4[CH2:34][CH2:35][CH:36]([CH2:37][C:38]([O:40]C(C)(C)C)=[O:39])[C:29]4=[CH:28][C:27]=3[CH:26]=2)=[CH:21][C:20]=1[C:47]([F:50])([F:49])[F:48])[CH:16]([CH3:18])[CH3:17]>O>[CH2:15]([C:19]1[CH:46]=[CH:45][C:22]([CH2:23][O:24][C:25]2[CH:33]=[CH:32][C:31]3[N:30]4[CH2:34][CH2:35][CH:36]([CH2:37][C:38]([OH:40])=[O:39])[C:29]4=[CH:28][C:27]=3[CH:26]=2)=[CH:21][C:20]=1[C:47]([F:50])([F:48])[F:49])[CH:16]([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 594DL-cysteineHCID 6422Trifluoroacetic acidHCID 67250244HCID 67250244, compound

Product 1

HCID 58329578HCID 58329578, compoundYield 71.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2-amino-3-mercaptopropanoic acid (0.042 g, 0.347 mmol) in TFA (600 pt, 7.79 mmol) was added to neat tert-butyl 2-(7-(4-isobutyl-3-(trifluoromethyl)benzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate (0.058 g, 0.116 mmol). The reaction mixture was stirred for 1 h at room temperature and then diluted with ice and water causing a tan solid to precipitate. The aqueous mixture was decanted off of the tan solid and the solid was rinsed with water. The solid was dried under vacuum to give the title compound (37 mg). LCMS m/z=446.7 [M+H]+; 1H NMR (400 MHz, CDCl3) δ ppm 0.89 (d, J=6.6 Hz, 6H), 1.87-1.98 (m, 1H), 2.16-2.26 (m, 1H), 2.53-2.82 (m, 5H), 3.53-3.62 (m, 1H), 3.92-4.00 (m, 1H), 4.06-4.14 (m, 1H), 5.13 (s, 2H), 6.01 (s, 1H), 6.77 (dd, J=8.7, 2.4 Hz, 1H), 7.07 (d, J=2.3 Hz, 1H), 7.19 (d, J=8.8 Hz, 1H), 7.47 (d, J=8.0 Hz, 1H), 7.67 (d, J=8.1 Hz, 1H), 7.75 (d, J=1.1 Hz, 1H).

Workup

  1. customto precipitate
  2. customThe aqueous mixture was decanted off of the tan solid
  3. washthe solid was rinsed with water
  4. customThe solid was dried under vacuum

Sources & evidence

ORD record
ord-93746c28fb0e4ea4920609c58da84ec4
Source dataset
uspto-grants-2013_04
Patent number
US08415484B2

Reaction notes

Loading…