Isopropyl chloroformate → HCID 69623815, compound

HRID 720248Notes

Reaction equation

HRID 720248 reaction equation
[CH2:1]([C:3]1([S:6]([NH:9][C:10]([C@@:12]2([NH:17][C:18]([C@@H:20]3[CH2:24][C@@H:23]([OH:25])[CH2:22][N:21]3[C:26](=[O:40])[C@@H:27]([NH:32][C:33]([O:35][C:36](C)([CH3:38])[CH3:37])=[O:34])[C:28]([CH3:31])([CH3:30])[CH3:29])=[O:19])[CH2:14][C@H:13]2[CH:15]=[CH2:16])=[O:11])(=[O:8])=[O:7])[CH2:5][CH2:4]1)[CH3:2].ClC(OC(C)C)=O.CCN(C(C)C)C(C)C>C(O)(C(F)(F)F)=O.C(Cl)Cl>[CH:36]([O:35][C:33](=[O:34])[NH:32][C@H:27]([C:26]([N:21]1[CH2:22][CH:23]([OH:25])[CH2:24][C@H:20]1[C:18](=[O:19])[NH:17][C@:12]1([C:10]([NH:9][S:6]([C:3]2([CH2:1][CH3:2])[CH2:4][CH2:5]2)(=[O:8])=[O:7])=[O:11])[CH2:14][C@H:13]1[CH:15]=[CH2:16])=[O:40])[C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:37])[CH3:38]

Participants

6

Reactant 3

HCID 7917Isopropyl chloroformateHCID 81531DiisopropylethylamineHCID 58738878HCID 58738878, compound

Product 1

HCID 69623815HCID 69623815, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 2(S)-[1 (R)-(1-ethyl-cyclopropanesulfonylaminocarbonyl)-2(S)-vinyl-cyclopropylcarbamoyl]-N-[N-Boc-amino-(S)-t-butyl-acetyl]-4(R)-hydroxy-pyrrolidine (585 mg, 1.0 mmol) in TFA (2 ml) and CH2Cl2 (2 ml) was stirred at room temperature for 1 h and concentrated in vacuo. The residue was dissolved in CH2Cl2 (5 ml) and isopropyl chloroformate (1.0M in toluene, 1.0 ml, 1.0 mmol), DIPEA (0.5 ml) were added. The resulting mixture was stirred at room temperature overnight and the solvent was removed in vacuo. The crude product was purified by flash column chromatograph (Biotage Flash 40M) eluted with EtOAc to provide the title compound (180 mg, 32%). MS 571 (M+H)+.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in CH2Cl2 (5 ml)
  3. customthe solvent was removed in vacuo
  4. customThe crude product was purified by flash column chromatograph (Biotage Flash 40M)
  5. washeluted with EtOAc

Sources & evidence

ORD record
ord-cec72955aba74df3b3bf0b71cbe6d1bf
Source dataset
uspto-grants-2006_11
Patent number
US07135462B2

Reaction notes

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