HCID 10445462, compound → HCID 18397107, compound

HRID 376234Notes

Reaction equation

HRID 376234 reaction equation
[N:1]([C@@H:4]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C@H:5]([OH:13])[C:6]([O:8][CH2:9][CH:10]([CH3:12])[CH3:11])=[O:7])=[N+:2]=[N-:3]>C(Cl)(Cl)Cl>[N:1]([C@@H:4]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C@H:5]([O:13][CH2:4][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:6]([O:8][CH2:9][CH:10]([CH3:12])[CH3:11])=[O:7])=[N+:2]=[N-:3]

Participants

3

Reactant 1

HCID 10445462HCID 10445462, compound

Product 1

HCID 18397107HCID 18397107, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Compound 11 (12.6 g, 47 mmol) was benzoylated, as described for 10, to yield (+)-12 (16 g, 88%):[a]D20=+54° (c 2, CHCl3); 1H NMR d 0.93 (d, J=9 Hz, 6 H), 1.75-1.91 (m, 1 H), 3.84-3.90 (m, 2 H), 5.15 (d, J=6 Hz, 1 H), 5.60 (d, J=6 Hz, 1 H), 7.34-7.61 (m, 8 H), 7.99-8.03 (m, 2 H).

Workup

  1. customto yield (+)-12 (16 g, 88%)

Sources & evidence

ORD record
ord-e9665e7380cc4878af09694a00860620
Source dataset
uspto-grants-2000_02
Patent number
US06020174

Reaction notes

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