Carbon tetrabromide → methyl 5-{2-[((2S)-2-{[(benzyloxy)carbonyl]amino}-3-bromopropyl)oxy]phenyl}-6-cyclohexyl-3-methyl-4H-thieno[3,2-b]pyrrole-2-carboxylate

HRID 1008998Notes

Reaction equation

HRID 1008998 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([CH2:40]O)[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.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([O-])([O-])=O.[K+].[K+].C(Br)(Br)(Br)[Br:68]>C(Cl)Cl>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([CH2:40][Br:68])[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

Participants

6

Reactant 4

HCID 11205Carbon tetrabromideHCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 67298563Methyl 5-{2-[((2R)-2-{[(benzyloxy)carbonyl]amino}-3-hydroxypropyl)oxy]phenyl}-6-cyclohexyl-3-methyl-4H-thieno[3,2-b]pyrrole-2-carboxylate

Product 1

HCID 67298840methyl 5-{2-[((2S)-2-{[(benzyloxy)carbonyl]amino}-3-bromopropyl)oxy]phenyl}-6-cyclohexyl-3-methyl-4H-thieno[3,2-b]pyrrole-2-carboxylateYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 5-{2-[((2R)-2-{[(benzyloxy)carbonyl]amino}-3-hydroxypropyl)oxy]phenyl}-6-cyclohexyl-3-methyl-4H-thieno[3,2-b]pyrrole-2-carboxylate and triphenylphosphine (2.27 eq.) were dissolved in DCM (0.02M) and K2CO3 (4.31 eq.) was added. To the stirred mixture CBr4 (2.22 eq.) was added and the yellowish reaction mixture was left stirring at RT for 3 h. All volatiles were evaporated i. vac. and the residual material was subjected to chromatography (PE:EtOAc, 8.5:1.5). The product was obtained as a yellowish sticky solid (86%). MS (ES+) m/z 639, 641 (M+H)+.

Workup

  1. customthe yellowish reaction mixture
  2. waitwas left
  3. customAll volatiles were evaporated i

Sources & evidence

ORD record
ord-68963da2782f43bd96a4ad4716e506ea
Source dataset
uspto-grants-2011_07
Patent number
US07973026B2

Reaction notes

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