1-Isocyanato-2-phenoxybenzene → 18-(2-Phenoxyphenylaminocarbonyloxy)-14-tert-butoxycarbonylamino-4-cyclopropylsulfonylaminocarbonyl-2,15-dioxo-3,16-diaza-12-oxatricyclo-[14.3.0.04,6]-nonadec-7-ene

HRID 500407Notes

Reaction equation

HRID 500407 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][O: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.[O:40]([C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][C:48]=1[N:53]=[C:54]=[O:55])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>>[O:40]([C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][C:48]=1[NH:53][C:54]([O: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]([CH3:36])([CH3:38])[CH3:37])=[O:33])[CH2:7][O: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[CH2:29][CH2:30]4)(=[O:26])=[O:27])=[O:23])([NH:17][C:18]2=[O:21])[CH2:15]3)[CH2:3]1)=[O:55])[C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1

Participants

3

Reactant 2

HCID 27333891-Isocyanato-2-phenoxybenzeneHCID 7226012718-Hydroxy-14-tert-butoxycarbonylamino-4-cyclopropylsulfonylaminocarbonyl-2,15-dioxo-3,16-diaza-12-oxatricyclo[14.3.0.04,6]-nonadec-7-ene

Product 1

HCID 8661208518-(2-Phenoxyphenylaminocarbonyloxy)-14-tert-butoxycarbonylamino-4-cyclopropylsulfonylaminocarbonyl-2,15-dioxo-3,16-diaza-12-oxatricyclo-[14.3.0.04,6]-nonadec-7-eneYield 15.3%

Procedure

Prepared by way of method III using 18-hydroxy-14-tert-butoxycarbonylamino-4-cyclopropylsulfonylaminocarbonyl-2,15-dioxo-3,16-diaza-12-oxatricyclo[14.3.0.04,6]-nonadec-7-ene (100 mg, 0.175 mmol) and 2-phenoxyphenyl isocyanate (94 mg, 0.53 mmol). The final trituration (diethyl ether/hexane) and filtration gave 21 mg (15%) of 18-(2-phenoxyphenylaminocarbonyloxy)-14-tert-butoxycarbonylamino-4-cyclopropylsulfonylaminocarbonyl-2,15-dioxo-3,16-diaza-12-oxatricyclo-[14.3.0.04,6]-nonadec-7-ene as a white powder: 99.2% pure (HPLC), MS m/z 780 (M−H)−, HRMS: calcd. 799.3337 and found 799.3325 (M+NH4)−, mp 151-153° C.

Workup

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

Sources & evidence

ORD record
ord-53b5a7370a654a489ccea14f410799b9
Source dataset
uspto-grants-2010_08
Patent number
US07772183B2

Reaction notes

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