Dicyclohexylcarbodiimide → HCID 121301725, compound

HRID 1775754Notes

Reaction equation

HRID 1775754 reaction equation
[C:1](=[O:46])([O:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[O:2][C@H:3]1[CH2:7][C@H:6]([N:8]2[CH:13]=[C:12]3[CH:14]=[C:15]([C:17]4[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:19][CH:18]=4)[O:16][C:11]3=[N:10][C:9]2=[O:28])[O:5][C@@H:4]1[CH2:29][O:30][Si](C(C)(C)C)(C)C.C1CCC(N=C=NC2CCCCC2)CC1.[NH:62]([C:70]([O:72][CH2:73][C:74]1[CH:79]=[CH:78][CH:77]=[CH:76][CH:75]=1)=[O:71])[C@H:63]([C:67](O)=[O:68])[CH:64]([CH3:66])[CH3:65]>CN(C1C=CN=CC=1)C.C1COCC1>[CH2:73]([O:72][C:70]([NH:62][C@@H:63]([CH:64]([CH3:66])[CH3:65])[C:67]([O:30][CH2:29][C@@H:4]1[C@@H:3]([O:2][C:1]([O:38][CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)=[O:46])[CH2:7][C@H:6]([N:8]2[CH:13]=[C:12]3[CH:14]=[C:15]([C:17]4[CH:18]=[CH:19][C:20]([CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:21][CH:22]=4)[O:16][C:11]3=[N:10][C:9]2=[O:28])[O:5]1)=[O:68])=[O:71])[C:74]1[CH:79]=[CH:78][CH:77]=[CH:76][CH:75]=1

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 726987N-Carbobenzoxy-L-valineHCID 86705082HCID 86705082, compound

Product 1

HCID 121301725HCID 121301725, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a 25 mL flask was added 53 mg (0.1 mmol) of (2R,3S,5R)-5-(2-oxo-6-(4-pentylphenyl)furo[2,3-d]pyrimidin-3 (2H)-yl)-2-((tert-butyldimethylsilyloxy)methyl)-tetrahydrofuran-3-yl benzyl carbonate, 12 mg (0.1 mmol) of DMAP, 31 mg (0.15 mmol) of DCC, 30 mg (0.12 mmol) of Cbz-Val-OH, and 5 mL of THF. The mixture was stirred at rt for 2 h.

Sources & evidence

ORD record
ord-924541ef016849269e38136c3778cada
Source dataset
uspto-grants-2016_02
Patent number
US09260469B2

Reaction notes

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