4-Methylmorpholine → (S,S)-Benthiavalicarb-isopropyl

HRID 1531407Notes

Reaction equation

HRID 1531407 reaction equation
[CH:1]([O:4][C:5]([NH:7][C@H:8]([C:12]([OH:14])=O)[CH:9]([CH3:11])[CH3:10])=[O:6])([CH3:3])[CH3:2].CN1CCOCC1.C(Cl)(=O)OCC(C)C.C1(C)C=CC(S(O)(=O)=O)=CC=1.[F:41][C:42]1[CH:53]=[CH:52][C:45]2[N:46]=[C:47]([C@@H:49]([NH2:51])[CH3:50])[S:48][C:44]=2[CH:43]=1>C1(C)C=CC=CC=1>[F:41][C:42]1[CH:53]=[CH:52][C:45]2[N:46]=[C:47]([C@@H:49]([NH:51][C:12]([C@@H:8]([NH:7][C:5](=[O:6])[O:4][CH:1]([CH3:2])[CH3:3])[CH:9]([CH3:10])[CH3:11])=[O:14])[CH3:50])[S:48][C:44]=2[CH:43]=1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 11063514(2S)-3-methyl-2-(((propan-2-yloxy)carbonyl)amino)butanoic acidHCID 86756512(S)-1-(6-fluoro-2-benzothiazolyl)ethylamine p-toluenesulfonate

Product 1

HCID 11700560(S,S)-Benthiavalicarb-isopropylYield 81.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

In 250 ml of toluene, 13.4 g (0.066 mol) of N-isopropoxycarbonyl-L-valine was dissolved. Thereto was added 14.3 g (0.144 mol) of N-methylmorpholine. Then was dropwise added at −10° C., 8.6 g (0.063 mol) of isobutyl chlorocarbonate. Thereto was added 22 g (0.06 mol) of (S)-1-(6-fluoro-2-benzothiazolyl)ethylamine p-toluenesulfonate. A reaction and a post-treatment were conducted in the same manner as in Reference Example 1, and the suspension of a solid in toluene was filtered at 70° C. to collect the solid. The solid was washed with water and toluene and dried to obtain 18.5 g (yield: 81.1%) of isopropyl {(S)-1-[(S)-1-(6-fluorobenzothiazol-2-yl)ethylcarbamoyl]-2-methylpropyl}carbamate. The compound obtained was confirmed for the structure by IR analysis and NMR analysis in comparison with its authentic material and identified.

Workup

  1. additionThen was dropwise added at −10° C.
  2. customA reaction
  3. filtrationwas filtered at 70° C.
  4. customto collect the solid
  5. washThe solid was washed with water and toluene
  6. customdried

Sources & evidence

ORD record
ord-1b7e878c203f463cb3d5033d92489d26
Source dataset
uspto-grants-2001_03
Patent number
US06197969B1

Reaction notes

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