Cyclohexanecarbonyl chloride → 18-Cyclohexanecarbonyloxy-14-tert-butoxycarbonylamino-4-cyclopropylsulfonylaminocarbonyl-2,15-dioxo-3,16-diaza-10-oxatricyclo-[14.3.0.04,6]-nonadec-7-ene

HRID 500381Notes

Reaction equation

HRID 500381 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.[CH:40]1([C:46](Cl)=[O:47])[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]1>>[CH:40]1([C:46]([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][O:10][CH2:11][CH:12]=[CH:13][CH:14]4[C:16]([C:22]([NH:24][S:25]([CH:28]5[CH2:29][CH2:30]5)(=[O:26])=[O:27])=[O:23])([NH:17][C:18]3=[O:21])[CH2:15]4)[CH2:3]2)=[O:47])[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]1

Participants

3

Reactant 2

HCID 75938Cyclohexanecarbonyl chlorideHCID 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 8661208118-Cyclohexanecarbonyloxy-14-tert-butoxycarbonylamino-4-cyclopropylsulfonylaminocarbonyl-2,15-dioxo-3,16-diaza-10-oxatricyclo-[14.3.0.04,6]-nonadec-7-eneYield 27%

Procedure

Prepared by way of method I of example 27 using 18-hydroxy-14-tert-butoxycarbonylamino-4-cyclopropylsulfonylaminocarbonyl-2,15-dioxo-3,16-diaza-10-oxatricyclo[14.3.0.04,6]-nonadec-7-ene (50 mg, 0.088 mmol) and cyclohexanecarbonyl chloride (35 μL, 0.26 mmol). The final trituration (diethyl ether/petroleum ether) and filtration gave 16 mg (27%) of 18-cyclohexanecarbonyloxy-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: 96.1% pure (HPLC), MS m/z 679 (M−H)−, HRMS: calcd. 679.3013 and found 679.3007 (M−H)−, mp 128-130° C.

Workup

  1. filtrationThe final trituration (diethyl ether/petroleum ether) and filtration

Sources & evidence

ORD record
ord-bba9a167c75f437496e0272c98b91bb7
Source dataset
uspto-grants-2010_08
Patent number
US07772183B2

Reaction notes

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