Sodium hydride → Methyl (7R)-7-{[(benzyloxy)carbonyl]amino}-13-cyclohexyl-10-methyl-7,8-dihydro-6H-thieno[2',3':4,5]pyrrolo[1,2-e][1,5]benzoxazocine-11-carboxylate

HRID 1008999Notes

Reaction equation

HRID 1008999 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([CH2:40]Br)[CH2:13][O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:21]1[NH:25][C:24]2[C:26]([CH3:33])=[C:27]([C:29]([O:31][CH3:32])=[O:30])[S:28][C:23]=2[C:22]=1[CH:34]1[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+]>CN(C=O)C>[CH2:1]([O:8][C:9]([NH:11][C@@H:12]1[CH2:40][N:25]2[C:24]3[C:26]([CH3:33])=[C:27]([C:29]([O:31][CH3:32])=[O:30])[S:28][C:23]=3[C:22]([CH:34]3[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]3)=[C:21]2[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[O:14][CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 67298840methyl 5-{2-[((2S)-2-{[(benzyloxy)carbonyl]amino}-3-bromopropyl)oxy]phenyl}-6-cyclohexyl-3-methyl-4H-thieno[3,2-b]pyrrole-2-carboxylate

Product 1

HCID 67298705Methyl (7R)-7-{[(benzyloxy)carbonyl]amino}-13-cyclohexyl-10-methyl-7,8-dihydro-6H-thieno[2',3':4,5]pyrrolo[1,2-e][1,5]benzoxazocine-11-carboxylateYield 45%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl 5-{2-[((2S)-2-{[(benzyloxy)carbonyl]amino}-3-bromopropyl)oxy]phenyl}-6-cyclohexyl-3-methyl-4H-thieno[3,2-b]pyrrole-2-carboxylate was dissolved in DMF (0.034M) and NaH (1.1 eq., 60% in mineral oil) was added. The mixture was left stirring at RT. After 30 min all volatiles were evaporated i. vac. The residual material was purified by chromatography (PE:EtOAc, 8.5:1.5). The product was obtained as a colourless solid (45%). MS (ES+) m/z 559 (M+H)+.

Workup

  1. waitThe mixture was left
  2. customAfter 30 min all volatiles were evaporated i
  3. customThe residual material was purified by chromatography (PE:EtOAc, 8.5:1.5)

Sources & evidence

ORD record
ord-7b356d088bec43748ec0e2297a1531fd
Source dataset
uspto-grants-2011_07
Patent number
US07973026B2

Reaction notes

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