DL-cysteine → HCID 58329578, compound

HRID 515690Notes

Reaction equation

HRID 515690 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 μL, 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-a0ef3125734241f2b58096f3ee9782d4
Source dataset
uspto-grants-2015_08
Patent number
US09108969B2

Reaction notes

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