Ammonium Chloride → HCID 69750714, compound

HRID 968226Notes

Reaction equation

HRID 968226 reaction equation
Cl[C:2]1[N:7]=[C:6]([S:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[F:16])[N:5]=[C:4]([NH2:17])[CH:3]=1.[NH2:18][C@@H:19]([CH2:21][OH:22])[CH3:20].[Cl-].[NH4+]>C(N(CC)CC)C>[NH2:17][C:4]1[N:5]=[C:6]([S:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[F:16])[N:7]=[C:2]([NH:18][C@H:19]([CH3:20])[CH2:21][OH:22])[CH:3]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 80308(R)-(-)-2-Amino-1-propanolHCID 4738497HCID 4738497, compound

Product 1

HCID 69750714HCID 69750714, compoundYield 62.4%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A solution of the product from example 4, step (b) (15 g), triethylamine (15 ml) and D-alaninol (10 g) was heated at 160° C. for 18 h. The reaction mixture was allowed to cool to room temperature and poured into aqueous ammonium chloride (11). The resultant white precipitate was purified by silica gel chromatography, eluting first with 1:1 DCM:ethyl acetate and then 3:1 DCM:methanol, giving the subtitled product as a yellow foam (10.7 g).

Workup

  1. customThe resultant white precipitate was purified by silica gel chromatography
  2. washeluting first with 1:1 DCM

Sources & evidence

ORD record
ord-e70d110cbdb14e888830b501894e08c9
Source dataset
uspto-grants-2005_10
Patent number
US06958344B2

Reaction notes

Loading…