methyl (S)-2-amino-3-(4-butoxy-phenyl)-propionate → tert-butyl (E)-(2S,3S)-3-[(S)-2-(4-butoxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-11-(2-heptyl-[1,3]dioxolan-2-yl)-2-hydroxy-2-(2-methoxy-ethyl)-undec-4-enoate

HRID 1779168Notes

Reaction equation

HRID 1779168 reaction equation
[CH2:1]([C:8]1([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]/[CH:19]=[CH:20]/[C@H:21]([C:35](N2[C@@H](C(C)C)C(C3C=CC=CC=3)(C3C=CC=CC=3)OC2=S)=[O:36])[C@@:22]([OH:34])([CH2:30][CH2:31][O:32][CH3:33])[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[O:12][CH2:11][CH2:10][O:9]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[NH2:58][C@@H:59]([CH2:64][C:65]1[CH:70]=[CH:69][C:68]([O:71][CH2:72][CH2:73][CH2:74][CH3:75])=[CH:67][CH:66]=1)[C:60]([O:62][CH3:63])=[O:61]>ClCCl>[CH2:72]([O:71][C:68]1[CH:67]=[CH:66][C:65]([CH2:64][C@H:59]([NH:58][C:35]([C@@H:21](/[CH:20]=[CH:19]/[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][C:8]2([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])[O:9][CH2:10][CH2:11][O:12]2)[C@@:22]([OH:34])([CH2:30][CH2:31][O:32][CH3:33])[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[O:36])[C:60]([O:62][CH3:63])=[O:61])=[CH:70][CH:69]=1)[CH2:73][CH2:74][CH3:75]

Participants

4

Reactant 2

HCID 68030835methyl (S)-2-amino-3-(4-butoxy-phenyl)-propionateHCID 90060091tert-butyl (E)-(2S,3S)-11-(2-heptyl-[1,3]dioxolan-2-yl)-2-hydroxy-3-((S)-4-isopropyl-5,5-diphenyl-2-thioxo-oxazolidine-3-carbonyl)-2-(2-methoxy-ethyl)-undec-4-enoate

Product 1

HCID 131734849tert-butyl (E)-(2S,3S)-3-[(S)-2-(4-butoxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-11-(2-heptyl-[1,3]dioxolan-2-yl)-2-hydroxy-2-(2-methoxy-ethyl)-undec-4-enoateYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

No. 6801291, tert-butyl (E)-(2S,3S)-11-(2-heptyl-[1,3]dioxolan-2-yl)-2-hydroxy-3-((S)-4-isopropyl-5,5-diphenyl-2-thioxo-oxazolidine-3-carbonyl)-2-(2-methoxy-ethyl)-undec-4-enoate (26.96 g, 35.84 mmol) and methyl (S)-2-amino-3-(4-butoxy-phenyl)-propionate were dissolved in dichloromethane, and the solvent was distilled off under reduced pressure. The resulting mixture was reacted at 50° C. for 2 days. After confirming the consumption of the starting materials by LCMS, n-hexane was added, and white powder was filtered. The solvent was distilled off under reduced pressure. The residue was purified with SP1 (SiO2 cartridge, 20% ethyl acetate/n-hexane, Rf=0.5) to obtain No. 5534988, tert-butyl (E)-(2S,3S)-3-[(S)-2-(4-butoxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-11-(2-heptyl-[1,3]dioxolan-2-yl)-2-hydroxy-2-(2-methoxy-ethyl)-undec-4-enoate (21.5 g, 79% yield).

Workup

  1. distillationthe solvent was distilled off under reduced pressure
  2. customThe resulting mixture was reacted at 50° C. for 2 days
  3. customthe consumption of the starting materials by LCMS, n-hexane
  4. additionwas added
  5. filtrationwhite powder was filtered
  6. distillationThe solvent was distilled off under reduced pressure
  7. customThe residue was purified with SP1 (SiO2 cartridge, 20% ethyl acetate/n-hexane, Rf=0.5)
  8. customto obtain No

Sources & evidence

ORD record
ord-ecde92cb44ff42e1a61ff14a5e83aa8f
Source dataset
uspto-grants-2016_02
Patent number
US09266853B2

Reaction notes

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