HCID 67272893, compound → HCID 67273353, compound

HRID 1698344Notes

Reaction equation

HRID 1698344 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([N:18]3[CH2:23][C@@H:22]([NH:24][C:25](=[O:38])[CH:26]([CH2:30][O:31]CC[Si](C)(C)C)[CH:27]([CH3:29])[CH3:28])[CH2:21][C@@H:20]([C:39](=[O:62])[N:40]([CH:59]4[CH2:61][CH2:60]4)[C:41]4[CH:42]=[CH:43][C:44]5[O:49][C:48]([CH3:51])([CH3:50])[C:47](=[O:52])[N:46]([CH2:53][CH2:54][CH2:55][O:56][CH3:57])[C:45]=5[CH:58]=4)[CH2:19]3)=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1>C(Cl)Cl.O>[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([N:18]3[CH2:23][C@@H:22]([NH:24][C:25](=[O:38])[CH:26]([CH2:30][OH:31])[CH:27]([CH3:29])[CH3:28])[CH2:21][C@@H:20]([C:39](=[O:62])[N:40]([CH:59]4[CH2:60][CH2:61]4)[C:41]4[CH:42]=[CH:43][C:44]5[O:49][C:48]([CH3:51])([CH3:50])[C:47](=[O:52])[N:46]([CH2:53][CH2:54][CH2:55][O:56][CH3:57])[C:45]=5[CH:58]=4)[CH2:19]3)=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 1

HCID 67272893HCID 67272893, compound

Product 1

HCID 67273353HCID 67273353, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (3R,5S)-3-{Cyclopropyl-[4-(3-methoxy-propyl)-2,2-dimethyl-3-oxo-3,4-di hydro-2H-benzo[1,4]oxazin-6-yl]-carbamoyl}-5-[3-methyl-2-(2-trimethylsilanyl-ethoxymethyl)-butyrylamino]-piperidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester in CH2Cl2 is added BF3 Et2O at room temperature, then the mixture is stirred at room temperature. After 1.5 h, the reaction mixture is diluted with H2O (10 mL) and extracted with CH2Cl2 (20 mL). The organic phase is washed with 5% aqueous KHSO4 (10 mL), 5% aqueous NaHCO3, H2O, and brine, then dried over Na2SO4. The solution is filtered and the solvent is evaporated in vacuo to give the title compound as white amorphous material. MS: 767 [M+H]+; tR (HPLC, ACQUITY UPLC™ BEH C18 1.7 μm, 50×2.1 mm; 5% CH3CN+0.1% TFA/H2O+0.1% TFA for 0.5 min then 5-100% CH3CN+0.1% TFA/H2O+0.1% TFA for 5 min then 100% CH3CN+0.1% TFA for 1.5 min, flow 0.5 ml/min): 1.55 min.

Workup

  1. extractionextracted with CH2Cl2 (20 mL)
  2. washThe organic phase is washed with 5% aqueous KHSO4 (10 mL), 5% aqueous NaHCO3, H2O, and brine
  3. dry with materialdried over Na2SO4
  4. filtrationThe solution is filtered
  5. customthe solvent is evaporated in vacuo

Sources & evidence

ORD record
ord-ab52beca48d54010a848ebabb23d2191
Source dataset
uspto-grants-2012_04
Patent number
US08163773B2

Reaction notes

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