Triethylamine → N-[3-(4,5,7-trifluorobenzothiazol-2-yl)propionyl]-N-methylglycine ethyl ester

HRID 1940611

Reaction equation

HRID 1940611 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:9])[CH2:6][NH:7][CH3:8])[CH3:3].Cl.CN(C)CCCN=C=NCC.[F:22][C:23]1[C:28]2[N:29]=[C:30]([CH2:32][CH2:33][C:34](O)=[O:35])[S:31][C:27]=2[C:26]([F:37])=[CH:25][C:24]=1[F:38].C(N(CC)CC)C>C(Cl)Cl>[CH2:2]([O:4][C:5](=[O:9])[CH2:6][N:7]([C:34](=[O:35])[CH2:33][CH2:32][C:30]1[S:31][C:27]2[C:26]([F:37])=[CH:25][C:24]([F:38])=[C:23]([F:22])[C:28]=2[N:29]=1)[CH3:8])[CH3:3]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 171173Ethyl N-methylaminoacetate hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 214635293-(4,5,7-Trifluorobenzothiazol-2-yl)propionic acid

Product 1

HCID 21463533N-[3-(4,5,7-trifluorobenzothiazol-2-yl)propionyl]-N-methylglycine ethyl esterYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To methylene chloride (10 ml) was added sarcosine ethyl ester hydrochloride (307 mg, 2 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (WSC.HCl; 422 mg, 2.2 mmol), 3-(4,5,7-trifluorobenzothiazol-2-yl)propionic acid (522 mg, 2 mmol) and triethylamine (220 mg, 2.2 mmol), and the mixture was stirred at room temperature for 15 hours. The resulting mixture was washed with water, dried and evaporated to yield a residue, which was purified on a silica gel column to give N-[3-(4,5,7-trifluorobenzothiazol-2-yl)propionyl]-N-methylglycine ethyl ester (610 mg, 85%) as an oil.

Workup

  1. washThe resulting mixture was washed with water
  2. customdried
  3. customevaporated
  4. customto yield a residue, which
  5. customwas purified on a silica gel column

Sources & evidence

ORD record
ord-ff383a306367473ba5c1ae34e4d81aa7
Source dataset
uspto-grants-1997_12
Patent number
US05700819

Linked notes

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