DL-cysteine → 2-(7-(3-Cyano-4-isopropoxybenzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic Acid

HRID 515718Notes

Reaction equation

NC(CS)C(O)=O.[C:8]([C:10]1[CH:11]=[C:12]([CH:35]=[CH:36][C:37]=1[O:38][CH:39]([CH3:41])[CH3:40])[CH2:13][O:14][C:15]1[CH:23]=[CH:22][C:21]2[N:20]3[CH2:24][CH2:25][CH:26]([CH2:27][C:28]([O:30]C(C)(C)C)=[O:29])[C:19]3=[CH:18][C:17]=2[CH:16]=1)#[N:9]>C(O)(C(F)(F)F)=O>[C:8]([C:10]1[CH:11]=[C:12]([CH:35]=[CH:36][C:37]=1[O:38][CH:39]([CH3:41])[CH3:40])[CH2:13][O:14][C:15]1[CH:23]=[CH:22][C:21]2[N:20]3[CH2:24][CH2:25][CH:26]([CH2:27][C:28]([OH:30])=[O:29])[C:19]3=[CH:18][C:17]=2[CH:16]=1)#[N:9]

Participants

Conditions

Temperature: 23 °C

Procedure

A solution of 2-amino-3-mercaptopropanoic acid (0.229 g, 1.889 mmol) in TFA (3.15 mL) was made and added to tert-butyl 2-(7-(3-cyano-4-isopropoxybenzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate (0.290 g, 0.630 mmol) in a 20 mL sealed scintillation vial and stirred at 23° C. for 15 min. After 15 min the solution was poured into ice water and stirred for 30 minutes. The resulting precipitate was collected by vacuum filtration, washed with water (2×5 mL) and n-Hexane (3×5 mL), and dried (vacuum oven) to give the title compound (0.202 g) as an off-white solid. LCMS m/z=405.5 [M+H]+.

Workup

customsealed scintillation vial
stirringstirred for 30 minutes
filtrationThe resulting precipitate was collected by vacuum filtration
washwashed with water (2×5 mL) and n-Hexane (3×5 mL)
customdried (vacuum oven)

Sources & evidence

ORD record: ord-7bba83ba9a0f45598bb226d70fecea8e
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09108969B2

Reaction notes

Loading…