methyl (S)-2-amino-3-(4-but-2-ynyloxy-phenyl)-propionate → tert-butyl (E)-(2S,3S)-3-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-2-hydroxy-2-propyl-10-(2-trimethylsilanyl-ethoxycarbonylamino)-dec-4-enoate

HRID 1779228Notes

Reaction equation

HRID 1779228 reaction equation
[OH:1][C@@:2]([CH2:51][CH2:52][CH3:53])([C@@H:10]([C:28](N1[C@@H](C(C)C)C(C2C=CC=CC=2)(C2C=CC=CC=2)OC1=S)=[O:29])/[CH:11]=[CH:12]/[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][NH:18][C:19]([O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])=[O:20])[C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[NH2:54][C@@H:55]([CH2:60][C:61]1[CH:66]=[CH:65][C:64]([O:67][CH2:68][C:69]#[C:70][CH3:71])=[CH:63][CH:62]=1)[C:56]([O:58][CH3:59])=[O:57]>ClCCl>[CH2:68]([O:67][C:64]1[CH:63]=[CH:62][C:61]([CH2:60][C@H:55]([NH:54][C:28]([C@@H:10](/[CH:11]=[CH:12]/[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][NH:18][C:19]([O:21][CH2:22][CH2:23][Si:24]([CH3:25])([CH3:27])[CH3:26])=[O:20])[C@@:2]([OH:1])([CH2:51][CH2:52][CH3:53])[C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4])=[O:29])[C:56]([O:58][CH3:59])=[O:57])=[CH:66][CH:65]=1)[C:69]#[C:70][CH3:71]

Participants

4

Reactant 2

HCID 58239373methyl (S)-2-amino-3-(4-but-2-ynyloxy-phenyl)-propionateHCID 90060242tert-butyl (E)-(2S,3S)-2-hydroxy-3-((S)-4-isopropyl-5,5-diphenyl-2-thioxo-oxazolidine-3-carbonyl)-2-propyl-10-(2-trimethylsilanyl-ethoxycarbonylamino)-dec-4-enoate

Product 1

HCID 131734869tert-butyl (E)-(2S,3S)-3-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-2-hydroxy-2-propyl-10-(2-trimethylsilanyl-ethoxycarbonylamino)-dec-4-enoateYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

tert-Butyl (E)-(2S,3S)-2-hydroxy-3-((S)-4-isopropyl-5,5-diphenyl-2-thioxo-oxazolidine-3-carbonyl)-2-propyl-10-(2-trimethylsilanyl-ethoxycarbonylamino)-dec-4-enoate (582 mg, 0.759 mmol) and methyl (S)-2-amino-3-(4-but-2-ynyloxy-phenyl)-propionate (376 mg, 1.52 mmol) were dissolved in dichloromethane (10 mL), and dichloromethane was then distilled off under reduced pressure. The obtained mixture was warmed at 40° C. for 41 hours. The reaction mixture was purified on Biotage (silica gel, n-hexane/ethyl acetate) to obtain 443 mg (0.0618 mmol, 81% yield) of tert-butyl (E)-(2S,3S)-3-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-2-hydroxy-2-propyl-10-(2-trimethylsilanyl-ethoxycarbonylamino)-dec-4-enoate.

Workup

  1. distillationdichloromethane was then distilled off under reduced pressure
  2. customThe reaction mixture was purified on Biotage (silica gel, n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-23b49cf6d6a8409ab8155b30c7d18f7b
Source dataset
uspto-grants-2016_02
Patent number
US09266853B2

Reaction notes

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