Acetic Acid → HCID 67266260, compound

HRID 1971311Notes

Reaction equation

[O:1]1[CH2:6][CH2:5][O:4][C:3]2[CH:7]=[C:8]([C:11]([NH:13][C@@H:14]3[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C@@H:16]([C:27]4[N:31]([CH2:32][CH2:33][O:34]C5CCCCO5)[C:30]5[CH:41]=[CH:42][CH:43]=[CH:44][C:29]=5[N:28]=4)[CH2:15]3)=[O:12])[CH:9]=[CH:10][C:2]1=2.C(O)(=O)C.C1COCC1>O>[O:1]1[CH2:6][CH2:5][O:4][C:3]2[CH:7]=[C:8]([C:11]([NH:13][C@@H:14]3[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C@@H:16]([C:27]4[N:31]([CH2:32][CH2:33][OH:34])[C:30]5[CH:41]=[CH:42][CH:43]=[CH:44][C:29]=5[N:28]=4)[CH2:15]3)=[O:12])[CH:9]=[CH:10][C:2]1=2

Participants

Conditions

Temperature: 45 °C

Procedure

(2R,4R)-tert-butyl 4-(2,3-dihydrobenzo[b][1,4]dioxine-6-carboxamido)-2-(1-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)-1H-benzo[d]imidazol-2-yl)piperidine-1-carboxylate (90 mg, 0.15 mmol) was added to a solution of acetic acid (2 mL), THF (1 mL) and water (0.5 mL) (4:2:1), the resulting solution was stirred at 45° C. for over night. The reaction mixture was concentrated to give a yellow oil as title compound (LC-MS: 523.2, t=2.3 min) for the next reaction without further purification.

Workup

concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record: ord-4a91d5c3e3874b549a20a7a9e123dc2d
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431597B2

Reaction notes

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