HCID 59386562, compound → HCID 59386550, compound

HRID 2358364Notes

Reaction equation

HRID 2358364 reaction equation
[C:1]1(C2C=CC=CC=2)[CH:6]=[CH:5][C:4]([C@@:7]2([O:55][CH3:56])[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]([NH:44][C@:45]3([C:50]([O:52][CH2:53][CH3:54])=[O:51])[CH2:47][C@H:46]3C=C)=[O:43])[CH2:8]2)=[CH:3][CH:2]=1>C(Cl)Cl.Cl[Ru](=C1N(C2C(C)=CC(C)=CC=2C)CCN1C1C(C)=CC(C)=CC=1C)(Cl)(=CC1C=CC=CC=1)[P](C1CCCCC1)(C1CCCCC1)C1CCCCC1>[C:1]1([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:2]=[CH:3][C:4]([C@@:7]2([O:55][CH3:56])[CH2:11][N:10]3[C@H:9]([C:42](=[O:43])[NH:44][C@:45]4([C:50]([O:52][CH2:53][CH3:54])=[O:51])[CH2:47][C@H:46]4[CH:32]=[CH:31][CH2:30][CH2:29][CH2:28][N:15]([S:16]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[N+:25]([O-:27])=[O:26])(=[O:17])=[O:18])[CH2:14][C@H:13]([NH:33][C:34]([O:36][C:37]([CH3:38])([CH3:40])[CH3:39])=[O:35])[C:12]3=[O:41])[CH2:8]2)=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 59386562HCID 59386562, compound

Product 1

HCID 59386550HCID 59386550, compoundYield 141%

Reagents, catalysts & solvents 2

HCID 178425456HCID 178425456, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of (1R,2S)-ethyl 1-((2S,4R)-4-(biphenyl-4-yl)-1-((S)-2-(tert-butoxycarbonylamino)-3-(2-nitro-N-(pent-4-enyl)phenylsulfonamido)propanoyl)-4-methoxypyrrolidine-2-carboxamido)-2-vinylcyclopropanecarboxylate (95 mg, 0.109 mmol) and Grubbs II (18.46 mg, 0.022 mmol) in DCM (200 mL) was refluxed for 4 h. The reaction mixture was then concentrated in vacuo. The residue was purified by Biotage eluting with 60% EtOAc/hexane to isolate 65 mg (71%) of (2R,6S,13aS,14aR,16aS,Z)-ethyl 2-(biphenyl-4-yl)-6-(tert-butoxycarbonylamino)-2-methoxy-8-(2-nitrophenylsulfonyl)-5,16-dioxo-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[n]pyrrolo[2,1-c][1,4,8]triazacyclopentadecine-14a-carboxylate as an off-white solid.

Workup

  1. temperaturewas refluxed for 4 h
  2. concentrationThe reaction mixture was then concentrated in vacuo
  3. customThe residue was purified by Biotage
  4. washeluting with 60% EtOAc/hexane

Sources & evidence

ORD record
ord-b451a5b4e9a94f768b7ddbe3b740f1fc
Source dataset
uspto-grants-2010_07
Patent number
US07763584B2

Reaction notes

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