Hydrochloric Acid → HCID 44454958, compound

HRID 968222Notes

Reaction equation

HRID 968222 reaction equation
Cl[C:2]1[N:10]=[C:9]([S:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:8]=[C:7]2[C:3]=1[NH:4][C:5](=[O:19])[NH:6]2.CN1CCCC1=O.O.Cl.[NH2:29][C@H:30]([CH2:32][OH:33])[CH3:31]>>[OH:33][CH2:32][C@H:30]([NH:29][C:2]1[N:10]=[C:9]([S:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:8]=[C:7]2[C:3]=1[NH:4][C:5](=[O:19])[NH:6]2)[CH3:31]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 13387N-methyl-2-pyrrolidoneHCID 80307L-AlaninolHCID 22288504HCID 22288504, compound

Product 1

HCID 44454958HCID 44454958, compoundYield 19.4%

Conditions

Temperature
100 °C

Procedure

A solution of the product from example 2, step (f) (0.1 g) in a mixture of alaninol (0.128 g), disopropylethylamine (0.35 ml) and N-methylpyrrolidinone (3 ml) was stirred at 100° C. for 48 h before pouring into H2O (75 ml). 2M HCl solution was then added to pH=2 and the light brown solid formed filtered and recrystallised from EtOH to afford the subtitle compound (22 mg, 19%)

Workup

  1. customthe light brown solid formed
  2. filtrationfiltered
  3. customrecrystallised from EtOH

Sources & evidence

ORD record
ord-d11a07ab6eea463ea25f5db68b1b0f0c
Source dataset
uspto-grants-2005_10
Patent number
US06958344B2

Reaction notes

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