Diisopropylcarbodiimide → HCID 131736946, compound

HRID 56831Notes

Reaction equation

HRID 56831 reaction equation
[Si:1]([O:8][CH:9]1[CH2:14][CH2:13][CH:12]([CH2:15][CH:16]([N:20]2[CH:25]=[C:24]([O:26][CH3:27])[C:23]([C:28]3[CH:33]=[C:32]([Cl:34])[CH:31]=[CH:30][C:29]=3[C:35]#[N:36])=[CH:22][C:21]2=[O:37])[C:17]([OH:19])=O)[CH2:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[NH2:38][C:39]1[CH:51]=[CH:50][C:42]([C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])=[CH:41][CH:40]=1.CC(C)N=C=NC(C)C>CN(C)C=O>[Si:1]([O:8][CH:9]1[CH2:10][CH2:11][CH:12]([CH2:15][CH:16]([N:20]2[CH:25]=[C:24]([O:26][CH3:27])[C:23]([C:28]3[CH:33]=[C:32]([Cl:34])[CH:31]=[CH:30][C:29]=3[C:35]#[N:36])=[CH:22][C:21]2=[O:37])[C:17]([NH:38][C:39]2[CH:51]=[CH:50][C:42]([C:43]([O:45][C:46]([CH3:47])([CH3:48])[CH3:49])=[O:44])=[CH:41][CH:40]=2)=[O:19])[CH2:13][CH2:14]1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 12734DiisopropylcarbodiimideHCID 233272Benzoic acid, 4-amino-, 1,1-dimethylethyl esterHCID 131736945HCID 131736945, compound

Product 1

HCID 131736946HCID 131736946, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

400 mg (734 μmol) of 3-(4-{[tert-butyl(dimethyl)silyl]oxy}cyclohexyl)-2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]propanoic acid (mixture of two racemic diastereomers), 142 mg (734 μmol) of tert-butyl 4-aminobenzoate, 104 mg (734 μmol) of Oxima and 114 μl (734 μmol) of DIC in 7.3 ml of dimethylformamide were reacted according to General Method 5B. The crude product was purified by flash chromatography (40 g cartridge, 40 ml/min, cyclohexane/ethyl acetate gradient). Yield: 341 mg (64% of theory)

Workup

  1. customThe crude product was purified by flash chromatography (40 g cartridge, 40 ml/min, cyclohexane/ethyl acetate gradient)

Sources & evidence

ORD record
ord-fdb78eefe36c4704be0973c457b34e99
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Reaction notes

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