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

HRID 1779229Notes

Reaction equation

HRID 1779229 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C@H:13]([NH:18][C:19]([C@@H:21](/[CH:34]=[CH:35]/[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][NH:41]C(OCC[Si](C)(C)C)=O)[C@@:22]([OH:33])([CH2:30][CH2:31][CH3:32])[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[O:20])[C:14]([O:16][CH3:17])=[O:15])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4]>[N+](C)([O-])=O.[Cl-].[Zn+2].[Cl-]>[NH2:41][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]/[CH:35]=[CH:34]/[C@H:21]([C:19](=[O:20])[NH:18][C@H:13]([C:14]([O:16][CH3:17])=[O:15])[CH2:12][C:9]1[CH:10]=[CH:11][C:6]([O:5][CH2:1][C:2]#[C:3][CH3:4])=[CH:7][CH:8]=1)[C@@:22]([OH:33])([CH2:30][CH2:31][CH3:32])[C:23]([O:25][C:26]([CH3:28])([CH3:29])[CH3:27])=[O:24]

Participants

4

Reactant 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-enoate

Product 1

HCID 90060365tert-butyl (E)-(2S,3S)-10-amino-3-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-2-hydroxy-2-propyl-dec-4-enoateYield 81%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 6375NitromethaneSolvent

Procedure

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 (298 mg, 0.415 mmol) was dissolved in nitromethane (1.5 mL), and zinc chloride (235 mg, 1.72 mmol) was then added at room temperature. The mixture was stirred for 4 hours, and then purified by preparative HPLC to obtain 192 mg (0.335 mmol, 81% yield) of tert-butyl (E)-(2S,3S)-10-amino-3-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-2-hydroxy-2-propyl-dec-4-enoate.

Workup

  1. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-77141676d9934a7ca5abc5c207f46185
Source dataset
uspto-grants-2016_02
Patent number
US09266853B2

Reaction notes

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