Water → HCID 86625965, compound

HRID 1971312Notes

Reaction equation

HRID 1971312 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[O:6]1[CH2:11][CH2:10][O:9][C:8]2[CH:12]=[C:13]([C:16]([NH:18][C@@H:19]3[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C@@H:21]([C:32]4[N:36]([CH2:37][CH2:38][OH:39])[C:35]5[CH:40]=[CH:41][CH:42]=[CH:43][C:34]=5[N:33]=4)[CH2:20]3)=[O:17])[CH:14]=[CH:15][C:7]1=2.O.C(OCC)(=O)C>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[O:6]1[CH2:11][CH2:10][O:9][C:8]2[CH:12]=[C:13]([C:16]([NH:18][C@@H:19]3[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C@@H:21]([C:32]4[N:36]([CH2:37][CH2:38][O:39][S:2]([CH3:1])(=[O:4])=[O:3])[C:35]5[CH:40]=[CH:41][CH:42]=[CH:43][C:34]=5[N:33]=4)[CH2:20]3)=[O:17])[CH:14]=[CH:15][C:7]1=2

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 31297Methanesulfonyl chlorideHCID 67266260HCID 67266260, compound

Product 1

HCID 86625965HCID 86625965, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

Methanesulfonyl chloride (51.3 mg, 0.448 mmol) was added to a solution of (2R,4R)-tert-butyl 4-(2,3-dihydrobenzo[b][1,4]dioxine-6-carboxamido)-2-(1-(2-hydroxyethyl)-1H-benzo[d]imidazol-2-yl)piperidine-1-carboxylate (78 mg, 0.15 mmol) and DMAP (3.5 mg) in pyridine (1 mL) at 0° C. and the resulting mixture was stirred at room temperature for 5 hours. Water and ethyl acetate were added to the reaction mixture. The organic layer was separated and dried over MgSO4 and concentrated to give a yellow solid, which was purified by Companion (ReadSep, 12 g, silica gel packed) with ethyl acetate/heptane from 30-70% to give title compound as a white solid 65 mg (73%). LC-MS: 601.1 (t=2.6 min).

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customto give a yellow solid, which
  5. customwas purified by Companion (ReadSep, 12 g, silica gel packed) with ethyl acetate/heptane from 30-70%

Sources & evidence

ORD record
ord-a2b97e75bb924c62a8d0da8110b095e6
Source dataset
uspto-grants-2013_04
Patent number
US08431597B2

Reaction notes

Loading…