1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 24971290, compound

HRID 2382220Notes

Reaction equation

HRID 2382220 reaction equation
[CH2:1]([C@H:7]1[C@H:10]([CH2:11][C@H:12]([OH:17])[CH2:13][CH2:14][CH:15]=[CH2:16])[O:9][C:8]1=[O:18])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].C(N=C=NCCCN(C)C)C.[CH:30]([NH:32][CH2:33][C:34](O)=[O:35])=[O:31]>CN(C)C1C=CN=CC=1.C1(C)C(C)=CC=CC=1>[CH:30]([NH:32][CH2:33][C:34]([O:17][C@H:12]([CH2:13][CH2:14][CH:15]=[CH2:16])[CH2:11][C@H:10]1[C@H:7]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[C:8](=[O:18])[O:9]1)=[O:35])=[O:31]

Participants

6

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 75606FormylglycineHCID 53798423(2R,3S,4S)-3-Hexyl-4-(2-hydroxy-hex-5-enyl)-oxetan-2-one

Product 1

HCID 24971290HCID 24971290, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 7237O-XyleneSolvent

Procedure

Prepared according to representative procedure described in Example 48 above (i.e., acylation) using hydroxy β-lactone 13j (15.0 mg, 0.059 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (14.8 mg, 0.077 mmol), 4-dimethylaminopyridine (8.71 mg, 0.071 mmol), 0.5 mL of xylene were azeotroped in vacuo for 1.0 h. After twelve hours the residue was then dissolved in CH2Cl2 (1.5 mL) and N-formyl glycine (9.12 mg, 0.089 mmol) was added. The resulting mixture was purified twice by chromatography (SiO2, gradient 10-40% EtOAc:hexanes) to afford β-lactone 17f (10.8 mg, 55%).

Workup

  1. customPrepared
  2. customwere azeotroped in vacuo for 1.0 h
  3. dissolutionAfter twelve hours the residue was then dissolved in CH2Cl2 (1.5 mL)
  4. customThe resulting mixture was purified twice by chromatography (SiO2, gradient 10-40% EtOAc:hexanes)

Sources & evidence

ORD record
ord-f7dac9b3747545b0b9cfb69bcdf5962c
Source dataset
uspto-grants-2012_09
Patent number
US08258321B2

Reaction notes

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