Hydrochloric Acid → HCID 59627206, compound

HRID 1523244Notes

Reaction equation

HRID 1523244 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]([CH2:15][CH2:16][C@:17]([NH:28][S@](C(C)(C)C)=O)([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)[CH2:18][CH:19]=[CH2:20])[C:11](=[O:14])[O:12][CH3:13])[CH3:9])=[CH:4][CH:3]=1.Cl.O1CCOCC1>>[NH2:28][C@@:17]([C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=1)([CH2:18][CH:19]=[CH2:20])[CH2:16][CH2:15][N:10]([C@H:8]([C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=1)[CH3:9])[C:11](=[O:14])[O:12][CH3:13]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 59627241HCID 59627241, compound

Product 1

HCID 59627206HCID 59627206, compound

Procedure

A 50-mL round-bottomed flask was charged with methyl (S)-1-(4-bromophenyl)ethyl((S)-3-((S)-1,1-dimethylethylsulfinamido)-3-(4-fluorophenyl)hex-5-enyl)carbamate (96 mg, 0.17 mmol) and 4 M HCl in dioxane (10 mL, 40 mmol) while cooling in an ice-water bath. The reaction mixture was concentrated to give crude methyl (S)-3-amino-3-(4-fluorophenyl)hex-5-enyl((S)-1-(4-bromophenyl)ethyl)carbamate, which was used to the next step without purification.

Workup

  1. temperaturewhile cooling in an ice-water bath
  2. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-cd9bfa770b314f478670afdc7c10d4b1
Source dataset
uspto-grants-2015_07
Patent number
US09079861B2

Reaction notes

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