Diisopropylcarbodiimide → HCID 67226568, compound

HRID 468597Notes

Reaction equation

HRID 468597 reaction equation
[OH:1][CH2:2][CH2:3][O:4][CH2:5][C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7].[O:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH:17]1[O:22][CH2:23][CH2:24][O:25][CH2:26][C:27](O)=[O:28].CC(C)N=C=NC(C)C>CN(C1C=CN=CC=1)C>[O:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH:17]1[O:22][CH2:23][CH2:24][O:25][CH2:26][C:27]([O:1][CH2:2][CH2:3][O:4][CH2:5][C:6]([O:8][CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)=[O:7])=[O:28]

Participants

5

Reactant 3

HCID 12734DiisopropylcarbodiimideHCID 67216757HCID 67216757, compoundHCID 68316807HCID 68316807, compound

Product 1

HCID 67226568HCID 67226568, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

A solution of the alcohol 4 (685 mg, 3.26 mmol), the acid 2 (932 mg, 4.57 mmol), DIC (680 μl, 4.57 mmol) and DMAP (39 mg, 0.32 mmol) was stirred overnight at room temperature. The mixture was then filtered and concentrated. Flash chromatography on silica gel (EtOAc/pentane 1/1) afforded compound 5 as an oil (1.06 g, 82%).

Workup

  1. filtrationThe mixture was then filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-63d62d34a6eb46a08651a1a3af96217f
Source dataset
uspto-grants-2014_01
Patent number
US08624044B2

Reaction notes

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