4-Fluorobenzoyl chloride → 18-(4-Fluorobenzoyloxy)-14-tert-butoxycarbonylamino-4-cyclopropylsulfonylaminocarbonyl-2,15-dioxo-3,16-diazatricyclo-[14.3.0.04,6]-nonadec-7-ene

HRID 500399Notes

Reaction equation

HRID 500399 reaction equation
[OH:1][CH:2]1[CH2:20][CH:19]2[N:4]([C:5](=[O:39])[CH:6]([NH:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH:12]=[CH:13][CH:14]3[C:16]([C:22]([NH:24][S:25]([CH:28]4[CH2:30][CH2:29]4)(=[O:27])=[O:26])=[O:23])([NH:17][C:18]2=[O:21])[CH2:15]3)[CH2:3]1.[F:40][C:41]1[CH:49]=[CH:48][C:44]([C:45](Cl)=[O:46])=[CH:43][CH:42]=1>>[F:40][C:41]1[CH:49]=[CH:48][C:44]([C:45]([O:1][CH:2]2[CH2:20][CH:19]3[N:4]([C:5](=[O:39])[CH:6]([NH:31][C:32]([O:34][C:35]([CH3:36])([CH3:38])[CH3:37])=[O:33])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH:12]=[CH:13][CH:14]4[C:16]([C:22]([NH:24][S:25]([CH:28]5[CH2:30][CH2:29]5)(=[O:27])=[O:26])=[O:23])([NH:17][C:18]3=[O:21])[CH2:15]4)[CH2:3]2)=[O:46])=[CH:43][CH:42]=1

Participants

3

Reactant 2

HCID 678794-Fluorobenzoyl chlorideHCID 68797769tert-butyl N-[4-(cyclopropylsulfonylcarbamoyl)-18-hydroxy-2,15-dioxo-3,16-diazatricyclo[14.3.0.04,6]nonadec-7-en-14-yl]carbamate

Product 1

HCID 7244536518-(4-Fluorobenzoyloxy)-14-tert-butoxycarbonylamino-4-cyclopropylsulfonylaminocarbonyl-2,15-dioxo-3,16-diazatricyclo-[14.3.0.04,6]-nonadec-7-eneYield 9.1%

Procedure

Prepared by way of method I using 18-hydroxy-14-tert-butoxycarbonylamino-4-cyclopropylsulfonylaminocarbonyl-2,15-dioxo-3,16-diazatricyclo[14.3.0.04,6]-nonadec-7-ene (100 mg, 0.176 mmol) and 4-fluorobenzoyl chloride (42 mg, 0.35 mmol). The final trituration (diethyl ether/hexane) and filtration gave 11 mg (9.1%) of 18-(4-fluorobenzoyloxy)-14-tert-butoxycarbonylamino-4-cyclopropylsulfonylaminocarbonyl-2,15-dioxo-3,16-diazatricyclo-[14.3.0.04,6]-nonadec-7-ene as a white powder: 95.0% pure (HPLC), MS m/z 689 (M−H)−, HRMS: calcd. 691.2813 and found 691.2827 (M+H)+, mp 154-156° C.

Workup

  1. customPrepared by way of method I
  2. filtrationThe final trituration (diethyl ether/hexane) and filtration

Sources & evidence

ORD record
ord-020d8e0278e94fbcb56e3761b7c5acdd
Source dataset
uspto-grants-2010_08
Patent number
US07772183B2

Reaction notes

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