Triethylamine → HCID 69651246, compound

HRID 1743273Notes

Reaction equation

HRID 1743273 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@:9]1([CH2:21][CH:22]2[CH2:27][CH2:26][N:25]([C:28]([O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])=[O:29])[CH2:24][CH2:23]2)[C:16](=[O:17])[N:15]2[C@@H:11]([S:12][CH2:13][C@H:14]2[C:18](=O)[NH2:19])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O>C1COCC1>[C:1]([O:5][C:6]([NH:8][C@@:9]1([CH2:21][CH:22]2[CH2:23][CH2:24][N:25]([C:28]([O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])=[O:29])[CH2:26][CH2:27]2)[C:16](=[O:17])[N:15]2[C@@H:11]([S:12][CH2:13][C@H:14]2[C:18]#[N:19])[CH2:10]1)=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 9845Trifluoroacetic anhydride2×HCID 69651241HCID 69651241, compound

Product 1

HCID 69651246HCID 69651246, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

295 mg of 2-trimethylsilanylethyl 4-((3R,6R,7aS)-6-tert-butoxycarbonylamino-3-carbamoyl-5-oxohexahydropyrrolo[2,1-b]thiazol-6-ylmethyl)piperidine-1-carboxylate were dissolved in 20 ml of THF. 166 μl of triethylamine and 91 μl of trifluoroacetic anhydride were successively added dropwise. The mixture was stirred for 1 h and then the same amounts of triethylamine and trifluoroacetic anhydride were again added. After stirring for a further hour, the mixture was partitioned between 150 ml of ethyl acetate and 150 ml of water. The organic phase was dried with MgSO4. The solvent was removed in vacuo and the residue was chromatographed on silica gel.

Workup

  1. stirringAfter stirring for a further hour
  2. customthe mixture was partitioned between 150 ml of ethyl acetate and 150 ml of water
  3. dry with materialThe organic phase was dried with MgSO4
  4. customThe solvent was removed in vacuo
  5. customthe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-43dc039f044f4bfbb5ec883abe78b580
Source dataset
uspto-grants-2006_03
Patent number
US07008957B2

Reaction notes

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