Triethylamine → (S)-4-[4-(4-Cyclopropylcarbamoyl-phenyl)-thiazol-2-ylcarbamoyl]-oxazolidine-3-carboxylic acid benzyl ester

HRID 737172Notes

Reaction equation

HRID 737172 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[C@H:15]([C:16]([OH:18])=O)[CH2:14][O:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.FC(F)(F)C(OC1C(F)=C(F)C(F)=C(F)C=1F)=O.FC(F)(F)C(O)=O.[NH2:51][C:52]1[S:53][CH:54]=[C:55]([C:57]2[CH:68]=[CH:67][C:60]([C:61]([NH:63][CH:64]3[CH2:66][CH2:65]3)=[O:62])=[CH:59][CH:58]=2)[N:56]=1>CN(C=O)C>[CH2:1]([O:8][C:9]([N:11]1[C@H:15]([C:16](=[O:18])[NH:51][C:52]2[S:53][CH:54]=[C:55]([C:57]3[CH:58]=[CH:59][C:60]([C:61](=[O:62])[NH:63][CH:64]4[CH2:66][CH2:65]4)=[CH:67][CH:68]=3)[N:56]=2)[CH2:14][O:13][CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 688328(-)-3-(Benzyloxycarbonyl)-4-oxazolidinecarboxylic acidHCID 4327891Pentafluorophenyl TrifluoroacetateHCID 866164294-(2-Amino-thiazol-4-yl)-n-cyclopropyl-benzamide trifluoroacetic acid salt

Product 1

HCID 57849690(S)-4-[4-(4-Cyclopropylcarbamoyl-phenyl)-thiazol-2-ylcarbamoyl]-oxazolidine-3-carboxylic acid benzyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(S)-Oxazolidine-3,4-dicarboxylic acid 3-benzyl ester (51.3 mg, 0.20 mmol) was dissolved in DMF (1.5 mL). Triethylamine (56 μL, 0.40 mmol) and pentafluorophenyl trifluoroacetate (35 μL, 0.20 mmol) were added, and the reaction was allowed to stir at ambient temperature for 25 minutes. Then 4-(2-Amino-thiazol-4-yl)-N-cyclopropyl-benzamide trifluoroacetic acid salt (148.8 mg, 0.40 mmol) was added, and the reaction was stirred at ambient temperature overnight. The reaction was filtered and purified by reverse phase HPLC to give the desired product. Yield 10.2 mg. MS: 493.1 (M+H+); H1 NMR (DMSO-d6): δ(ppm) 0.52-0.74 (m, 4H), 4.05-4.37 (m, 2H), 4.58-4.69 (m, 1H), 4.90-5.17 (m, 4H), 7.00-7.45 (m, 4H), 7.72-7.98 (m, 5H), 8.37-8.48 (m, 1H), 12.48-12.51 (s, 1H).

Workup

  1. stirringthe reaction was stirred at ambient temperature overnight
  2. filtrationThe reaction was filtered
  3. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-0f5490f86f6a4bfca8a7be48ded3d6ce
Source dataset
uspto-grants-2009_09
Patent number
US07595398B2

Reaction notes

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