DL-cysteine → HCID 58329594, compound

HRID 1964110Notes

Reaction equation

HRID 1964110 reaction equation
NC(C(O)=O)CS.[Cl:8][C:9]1[CH:36]=[CH:35][C:12]([CH2:13][O:14][C:15]2[CH:23]=[CH:22][C:21]3[N:20]4[CH2:24][CH2:25][CH:26]([CH2:27][C:28]([O:30]C(C)(C)C)=[O:29])[C:19]4=[CH:18][C:17]=3[CH:16]=2)=[CH:11][C:10]=1[C:37]([F:40])([F:39])[F:38]>C(O)(C(F)(F)F)=O>[Cl:8][C:9]1[CH:36]=[CH:35][C:12]([CH2:13][O:14][C:15]2[CH:23]=[CH:22][C:21]3[N:20]4[CH2:24][CH2:25][CH:26]([CH2:27][C:28]([OH:30])=[O:29])[C:19]4=[CH:18][C:17]=3[CH:16]=2)=[CH:11][C:10]=1[C:37]([F:40])([F:38])[F:39]

Participants

4

Reactant 2

HCID 594DL-cysteineHCID 67251754HCID 67251754, compound

Product 1

HCID 58329594HCID 58329594, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of D,L-cysteine (0.056 g, 0.460 mmol) in TFA (0.9 mL) was added tert-butyl 2-(7-(4-chloro-3-(trifluoromethyl)benzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate (0.079 g, 0.153 mmol). The reaction was stirred for 2 h and poured into ice water. The resulting precipitate was collected by vacuum filtration to give the title compound as a solid. LCMS m/z=424.1 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 2.14-2.27 (m, 1H), 2.55 (dd, J=16.29, 7.96 Hz, 1H), 2.64-2.72 (m, 1H), 2.72-2.82 (m, 1H), 3.51-3.64 (m, 1H), 3.90-4.01 (m, 1H), 4.05-4.17 (m, 1H), 5.18 (s, 2H), 6.01 (s, 1H), 6.78 (dd, J=8.72, 2.40 Hz, 1H), 7.07 (d, J=2.40 Hz, 1H), 7.20 (d, J=8.72 Hz, 1H), 7.69-7.81 (m, 2H), 7.92 (s, 1H), 12.24 (bs, 1H).

Workup

  1. filtrationThe resulting precipitate was collected by vacuum filtration

Sources & evidence

ORD record
ord-ac25711e3fd6414ea60fb02895395eb1
Source dataset
uspto-grants-2013_04
Patent number
US08415484B2

Reaction notes

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