Methyl 2-isocyanatobenzoate → 18-(2-Carbomethoxyphenylaminocarbonyloxy)-14-tert-butoxycarbonylamino-4-cyclopropylsulfonylaminocarbonyl-2,15-dioxo-3,16-diaza-10-oxatricyclo-[14.3.0.04,6]-nonadec-7-ene

HRID 500406Notes

Reaction equation

HRID 500406 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][O: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.[C:40]([C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=1[N:50]=[C:51]=[O:52])([O:42][CH3:43])=[O:41]>>[C:40]([C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=1[NH:50][C:51]([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][CH2:8][CH2:9][O: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:52])([O:42][CH3:43])=[O:41]

Participants

3

Reactant 2

HCID 519494Methyl 2-isocyanatobenzoateHCID 7226012218-Hydroxy-14-tert-butoxycarbonylamino-4-cyclopropylsulfonylaminocarbonyl-2,15-dioxo-3,16-diaza-10-oxatricyclo[14.3.0.04,6]-nonadec-7-ene

Product 1

HCID 7244536918-(2-Carbomethoxyphenylaminocarbonyloxy)-14-tert-butoxycarbonylamino-4-cyclopropylsulfonylaminocarbonyl-2,15-dioxo-3,16-diaza-10-oxatricyclo-[14.3.0.04,6]-nonadec-7-eneYield 41%

Procedure

Prepared by way of method III using 18-hydroxy-14-tert-butoxycarbonylamino-4-cyclopropylsulfonylaminocarbonyl-2,15-dioxo-3,16-diaza-10-oxatricyclo[14.3.0.04,6]-nonadec-7-ene (100 mg, 0.175 mmol) and 2-carbomethoxyphenyl isocyanate (62 mg, 0.35 mmol). The final trituration (diethyl ether/hexane) and filtration gave 53 mg (41%) of 18-(2-carbomethoxyphenylaminocarbonyloxy)-14-tert-butoxycarbonylamino-4-cyclopropylsulfonylaminocarbonyl-2,15-dioxo-3,16-diaza-10-oxatricyclo-[14.3.0.04,6]-nonadec-7-ene as a white powder: 99.6% pure (HPLC), MS m/z 746 (M−H)−, HRMS: calcd. 786.2423 and found 786.2436 (M−H+K)−, mp 147-149° C.

Workup

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

Sources & evidence

ORD record
ord-7f0b3e636a6b4357a80a24c251cfd54f
Source dataset
uspto-grants-2010_08
Patent number
US07772183B2

Reaction notes

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