Isobutyl chloroformate → HCID 67506537, compound

HRID 1791960Notes

Reaction equation

HRID 1791960 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([N:13]2[CH2:18][CH2:17][CH:16]([C:19]3[O:20][C:21]4[CH:27]=[CH:26][C:25]([C:28](O)=[O:29])=[CH:24][C:22]=4[N:23]=3)[CH2:15][CH2:14]2)[CH2:10][C@H:9]1[C:31]([N:33]1[CH2:37][CH2:36][S:35][CH2:34]1)=[O:32])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.Cl.C(C1C=CC2OC(C3CCN([C@@H]4CN[C@H](C(N5CCSC5)=O)C4)CC3)=[N:48]C=2C=1)(O)=O.C(Cl)(=O)OCC(C)C.N.CO>O1CCCC1.O.C(N(CC)CC)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([N:13]2[CH2:18][CH2:17][CH:16]([C:19]3[O:20][C:21]4[CH:27]=[CH:26][C:25]([C:28](=[O:29])[NH2:48])=[CH:24][C:22]=4[N:23]=3)[CH2:15][CH2:14]2)[CH2:10][C@H:9]1[C:31]([N:33]1[CH2:37][CH2:36][S:35][CH2:34]1)=[O:32])=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

8

Reactant 4

HCID 62365Isobutyl chloroformateHCID 21705897Ammonia methanolHCID 67506455HCID 67506455, compoundHCID 67507069HCID 67507069, compound

Product 1

HCID 67506537HCID 67506537, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

3-{(2S,4S)-1-tert-Butoxycarbonyl-4-[4-(5-carboxy-2-benzoxazolyl)piperidino]-2-pyrrolidinylcarbonyl}-1,3-thiazolidine [product of Example 310 (1), 1.06 g] was dissolved in tetrahydrofuran (5 mL), and triethylamine (0.279 mL) and isobutyl chlorocarbonate (0.263 mL) were added thereto under ice-cooling. The mixture was stirred at room temperature for 30 min. A solution of 7 mol/L ammonia-methanol (1 mL) was added to the reaction mixture, and the mixture was stirred at room temperature for 15 hr. Water was added to the reaction mixture, and the mixture was extracted with chloroform. The extract was dried and concentrated under reduced pressure. The residue was purified by silica gel chromatography to give 3-{(2S,4S)-1-tert-butoxycarbonyl-4-[4-(5-carbamoyl-2-benzoxazolyl)piperidino]-2-pyrrolidinylcarbonyl}-1,3-thiazolidine (345 mg) as a white powder.

Workup

  1. temperatureunder ice-cooling
  2. stirringthe mixture was stirred at room temperature for 15 hr
  3. extractionthe mixture was extracted with chloroform
  4. customThe extract was dried
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-e5f8a227751f4bb0aad3aad7cf9cb409
Source dataset
uspto-grants-2006_07
Patent number
US07074794B2

Reaction notes

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