Methanol → HCID 59386557, compound

HRID 2358363Notes

Reaction equation

HRID 2358363 reaction equation
[C:1]1([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[CH:6]=[CH:5][C:4]([C@@:7]2([O:46][CH3:47])[CH2:11][N:10]([C:12](=[O:41])[C@@H:13]([NH:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:14][N:15]([CH2:28][CH2:29][CH2:30][CH:31]=[CH2:32])[S:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[N+:25]([O-:27])=[O:26])(=[O:18])=[O:17])[C@H:9]([C:42]([O:44]C)=[O:43])[CH2:8]2)=[CH:3][CH:2]=1.CO.O>O1CCCC1>[C:1]1([C:48]2[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=2)[CH:6]=[CH:5][C:4]([C@@:7]2([O:46][CH3:47])[CH2:11][N:10]([C:12](=[O:41])[C@@H:13]([NH:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:14][N:15]([CH2:28][CH2:29][CH2:30][CH:31]=[CH2:32])[S:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[N+:25]([O-:27])=[O:26])(=[O:17])=[O:18])[C@H:9]([C:42]([OH:44])=[O:43])[CH2:8]2)=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 962WaterHCID 59386542HCID 59386542, compound

Product 1

HCID 59386557HCID 59386557, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (2S,4R)-methyl 4-(biphenyl-4-yl)-1-((S)-2-(tert-butoxycarbonylamino)-3-(2-nitro-N-(pent-4-enyl)phenylsulfonamido)propanoyl)-4-methoxypyrrolidine-2-carboxylate (185 mg, 0.246 mmol) and LiOH monohydrate (118 mg, 4.93 mmol) in tetrahydrofuran (2 mL)/MeOH (0.5 mL)/Water (1 mL) was stirred at rt for 18 h. The reaction mixture was then concentrated in vacuo and diluted with 5 mL of water. It was then washed with ether. The aqueous phase was adjusted to pH=4 using 1N HCl. It was then extracted with EtOAc, dried over MgSO4, filtered and concentrated in vacuo to yield 160 mg (87%) of (2S,4R)-4-(biphenyl-4-yl)-1-((S)-2-(tert-butoxycarbonylamino)-3-(2-nitro-N-(pent-4-enyl)phenylsulfonamido)propanoyl)-4-methoxypyrrolidine-2-carboxylic acid as a white solid.

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. additiondiluted with 5 mL of water
  3. washIt was then washed with ether
  4. extractionIt was then extracted with EtOAc
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6b7a0d56c9c047328cf704cd93374b76
Source dataset
uspto-grants-2010_07
Patent number
US07763584B2

Reaction notes

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