1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (R)-1-((2S,3S)-3-hexyl-4-oxooxetan-2-yl)hept-5-en-2-yl 2-methanamidoethanoate

HRID 2382221Notes

Reaction equation

HRID 2382221 reaction equation
[CH2:1]([C@H:7]1[C@H:10]([CH2:11][C@H:12]([OH:18])[CH2:13][CH2:14][CH:15]=[CH:16][CH3:17])[O:9][C:8]1=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].C(N=C=NCCCN(C)C)C.[CH:31]([NH:33][CH2:34][C:35](O)=[O:36])=[O:32]>CN(C)C1C=CN=CC=1.C1(C)C(C)=CC=CC=1>[CH:31]([NH:33][CH2:34][C:35]([O:18][C@H:12]([CH2:13][CH2:14][CH:15]=[CH:16][CH3:17])[CH2:11][C@H:10]1[C@H:7]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[C:8](=[O:19])[O:9]1)=[O:36])=[O:32]

Participants

6

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 75606FormylglycineHCID 87625200HCID 87625200, compound

Product 1

HCID 87624001(R)-1-((2S,3S)-3-hexyl-4-oxooxetan-2-yl)hept-5-en-2-yl 2-methanamidoethanoateYield 57.1%

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 13k (15.6 mg, 0.058 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (14.4 mg, 0.075 mmol), 4-dimethylaminopyridine (8.7 mg, 0.070 mmol), 0.5 mL of xylene were azeotroped in vacuo for 1.0 h. The residue was then dissolved in CH2Cl2 (1.5 mL) and N-formyl glycine (9.0 mg, 0.087 mmol) was added. After twelve hours resulting mixture was purified by chromatography (SiO2, gradient 10-40% EtOAc:hexanes) to afford β-lactone 17g (11.7 mg, 57%).

Workup

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

Sources & evidence

ORD record
ord-9025993cc1364b88a93e616116fc66db
Source dataset
uspto-grants-2012_09
Patent number
US08258321B2

Reaction notes

Loading…