Methanol → HCID 59386559, compound

HRID 2358365Notes

Reaction equation

HRID 2358365 reaction equation
[C:1]1([C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)[CH:6]=[CH:5][C:4]([C@@:7]2([O:53][CH3:54])[CH2:24][N:23]3[C@H:9]([C:10](=[O:52])[NH:11][C@:12]4([C:47]([O:49]CC)=[O:48])[CH2:46][C@H:13]4[CH:14]=[CH:15][CH2:16][CH2:17][CH2:18][N:19]([S:34]([C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=4[N+:43]([O-:45])=[O:44])(=[O:36])=[O:35])[CH2:20][C@H:21]([NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C:22]3=[O:25])[CH2:8]2)=[CH:3][CH:2]=1.O.CO>O1CCCC1>[C:1]1([C:55]2[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=2)[CH:6]=[CH:5][C:4]([C@@:7]2([O:53][CH3:54])[CH2:24][N:23]3[C@H:9]([C:10](=[O:52])[NH:11][C@:12]4([C:47]([OH:49])=[O:48])[CH2:46][C@H:13]4[CH:14]=[CH:15][CH2:16][CH2:17][CH2:18][N:19]([S:34]([C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=4[N+:43]([O-:45])=[O:44])(=[O:36])=[O:35])[CH2:20][C@H:21]([NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:31])[CH3:32])=[O:28])[C:22]3=[O:25])[CH2:8]2)=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 962WaterHCID 59386550HCID 59386550, compound

Product 1

HCID 59386559HCID 59386559, compoundYield 25.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture 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 (60 mg, 0.071 mmol) and LiOH monohydrate (34.0 mg, 1.419 mmol) in tetrahydrofuran (2 mL)/water (0.5 mL)/MeOH (1 mL) was stirred at rt for 18 h. It was then concentrated in vacuo and partitioned between water and ether. The aqueous phase was adjusted to pH=4 using 1N HCl and extracted with EtOAc. The organic phase was then dried over MgSO4, filtered, and concentrated to isolate 52 mg of the crude product as an off-white solid. Purification by preparative HPLC gave 15 mg of (2R,6S,13aS,14aR,16aS,Z)-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-carboxylic acid as a white solid.

Workup

  1. concentrationIt was then concentrated in vacuo
  2. custompartitioned between water and ether
  3. extractionextracted with EtOAc
  4. dry with materialThe organic phase was then dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto isolate 52 mg of the crude product as an off-white solid
  8. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-a8f340d5fd6d4931b8144922d623dfd4
Source dataset
uspto-grants-2010_07
Patent number
US07763584B2

Reaction notes

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