Triethylamine → HCID 59571157, compound

HRID 389220Notes

Reaction equation

HRID 389220 reaction equation
[CH2:1]([C@@H:6]1[CH2:10][CH2:9][CH2:8][C@H:7]1[OH:11])[CH2:2][CH2:3][CH:4]=[CH2:5].[CH2:12]1[C:17](=[O:18])[N:16]([O:19][C:20](ON2C(=O)CCC2=O)=[O:21])[C:14](=[O:15])[CH2:13]1.CCN(CC)CC>CC#N>[CH2:1]([C@@H:6]1[CH2:10][CH2:9][CH2:8][C@H:7]1[O:11][C:20]([O:19][N:16]1[C:17](=[O:18])[CH2:12][CH2:13][C:14]1=[O:15])=[O:21])[CH2:2][CH2:3][CH:4]=[CH2:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 676246Di(succinimido) carbonateHCID 58158112HCID 58158112, compound

Product 1

HCID 59571157HCID 59571157, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of (1R,2R)-2-pent-4-en-1-ylcyclopentanol (105 mg, 0.68 mmol) in MeCN (1.4 mL) was added N,N′-disuccinimidyl carbonate (174 mg, 0.68 mmol) and Et3N (0.19 mL, 1.36 mmol) and the mixture was stirred at 40 C for 20 hours. The reaction mixture was cooled, concentrated and purified by silica chromatography (gradient elution 0 to 100% EtOAc in hexane). LCMS (M+Na)+=318.1.

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated
  3. custompurified by silica chromatography (gradient elution 0 to 100% EtOAc in hexane)

Sources & evidence

ORD record
ord-05951073f9d145f7a26563e9f8212722
Source dataset
uspto-grants-2013_02
Patent number
US08377874B2

Reaction notes

Loading…