Hydrochloric Acid → HCID 68847229, compound

HRID 45628Notes

Reaction equation

HRID 45628 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]([N:28]3[C@H:33]([CH2:34][CH:35]([CH3:37])[CH3:36])[C:32](=[O:38])[NH:31][C@H:30]([CH:39]4[CH2:47][C:46]5[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=5)[CH2:40]4)[C:29]3=[O:48])[C:11]([NH:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[O:20]CC3C=CC=CC=3)=[O:12])=[CH:9][C:4]=2[CH:3]=[CH:2]1.B(Br)(Br)Br.Cl>ClCCl>[S:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]([N:28]3[C@H:33]([CH2:34][CH:35]([CH3:36])[CH3:37])[C:32](=[O:38])[NH:31][C@H:30]([CH:39]4[CH2:47][C:46]5[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=5)[CH2:40]4)[C:29]3=[O:48])[C:11]([NH:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[OH:20])=[O:12])=[CH:9][C:4]=2[CH:3]=[CH:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 25134Boron tribromideHCID 68847439(2RS)-2-(1-benzothien-5-yl)-2-[(3R,6R)-3-(2,3-dihydro-1H-inden-2-yl)-6-isobutyl-2,5-dioxopiperazin-1-yl]-N-(2-benzyloxyphenyl)ethanamide

Product 1

HCID 68847229HCID 68847229, compoundYield 24.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

(2RS)-2-(1-benzothien-5-yl)-2-[(3R,6R)-3-(2,3-dihydro-1H-inden-2-yl)-6-isobutyl-2,5-dioxopiperazin-1-yl]-N-(2-benzyloxyphenyl)ethanamide (1.0 g) was dissolved in dichloromethane (5 ml) and to this was added dropwise a 1.0M solution of BBr3 in dichloromethane (2.0 ml). The reaction mixture was stirred at room temperature for 2 hours. To the reaction mixture was added 1N hydrochloric acid (30 ml) and dichloromethane (20 ml). The phases were separated and the organic phase was washed with 1N hydrochloric acid (30 ml) and brine (30 ml). The organic phase was dried over MgSO4 and evaporated in vacuo. The residue was purified by Biotage™ flash column chromatography, eluting with 3:2 ethyl acetate:cyclohexane. The required fractions were combined and evaporated in vacuo to give (2RS)-2-(1-benzothien-5-yl)-2-[(3R,6R)-3-(2,3-dihydro-1H-inden-2-yl)-6-isobutyl-2,5-dioxopiperazin-1-yl]-N-(2-hydroxyphenyl)ethanamide (210 mg).

Workup

  1. customThe phases were separated
  2. washthe organic phase was washed with 1N hydrochloric acid (30 ml) and brine (30 ml)
  3. dry with materialThe organic phase was dried over MgSO4
  4. customevaporated in vacuo
  5. customThe residue was purified by Biotage™ flash column chromatography
  6. washeluting with 3:2 ethyl acetate
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-59f18ed4145f4d2b8d5b32a8a2036756
Source dataset
uspto-grants-2013_09
Patent number
US08541579B2

Reaction notes

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