Dicyclohexylcarbodiimide → HCID 11124529, compound

HRID 1007875Notes

Reaction equation

HRID 1007875 reaction equation
[CH2:1]([C:3]1([OH:29])[C:26]2[CH:25]=[C:24]3[N:10]([CH2:11][C:12]4[C:13]3=[N:14][C:15]3[CH:16]=[C:17]([F:23])[C:18]([F:22])=[CH:19][C:20]=3[CH:21]=4)[C:9](=[O:27])[C:8]=2[CH2:7][O:6][C:5](=[O:28])[CH2:4]1)[CH3:2].[C:30]([NH:37][CH2:38][C:39](O)=[O:40])([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[C:33]([O:32][C:30]([NH:37][CH2:38][C:39]([O:29][C:3]1([CH2:1][CH3:2])[C:26]2[CH:25]=[C:24]3[N:10]([CH2:11][C:12]4[C:13]3=[N:14][C:15]3[CH:16]=[C:17]([F:23])[C:18]([F:22])=[CH:19][C:20]=3[CH:21]=4)[C:9](=[O:27])[C:8]=2[CH2:7][O:6][C:5](=[O:28])[CH2:4]1)=[O:40])=[O:31])([CH3:36])([CH3:35])[CH3:34]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 78288N-(tert-butoxycarbonyl)glycineHCID 9822187HCID 9822187, compound

Product 1

HCID 11124529HCID 11124529, compoundYield 14%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

A mixture of 5-ethyl-9,10-difluoro-5-hydroxy-1,4,5,13-tetrahydro-3H,15H-oxepino[3′,4′:6,7]indolizino[1,2-b]quinoline-3,15-dione (200 mg, 0.526 mmol, example 18), N-Boc-glycine (185 mg, 1.051 mmol) and a catalytic quantity of 4-dimethylaminopyridine (20 mg) in anhydrous pyridine (10 ml) is treated at 0° C. and under argon with dicyclohexylcarbodiimide (239 mg, 1.16 mmol), then agitated at ambient temperature for 48 hours. The volatiles are driven off under vacuum and the residue is chromatographed (SiO2, 1% methanol in chloroform) in order to produce the desired intermediate (40 mg, 14%), a yellow solid.

Workup

  1. customthe residue is chromatographed (SiO2, 1% methanol in chloroform) in order

Sources & evidence

ORD record
ord-54b06bc2fbea46ceb2eb287e9b3f29d8
Source dataset
uspto-grants-2004_09
Patent number
US06797715B1

Reaction notes

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