Isopropylamine → HCID 54508459, compound

HRID 257115Notes

Reaction equation

HRID 257115 reaction equation
[C:1]([O:7][C@H:8]([CH2:20][C@H:21]1[C@H:24]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[C:23](=[O:31])[O:22]1)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])(=[O:6])[CH2:2][C:3]([OH:5])=O.CN(C(O[N:40]1N=N[C:42]2C=CC=[CH:46][C:41]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N)(C)C>C(#N)C>[CH2:25]([C@@H:24]1[C:23](=[O:31])[O:22][C@H:21]1[CH2:20][C@@H:8]([O:7][C:1](=[O:6])[CH2:2][C:3]([NH:40][CH:41]([CH3:46])[CH3:42])=[O:5])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]

Participants

5

Reactant 3

HCID 6363IsopropylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86747359HCID 86747359, compound

Product 1

HCID 54508459HCID 54508459, compoundYield 84.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 33.5 mg of (S)-1-[[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]methyl]dodecyl hydrogen malonate (Example N) in 2 ml of acetonitrile was treated with 60 mg of HBTU and 75 mg of iso-propylamine. After stirring the reaction mixture was filtered, the filtrate was concentrated and the residue was chromatographed on silica gel with hexane/methylene chloride/ethyl acetate (2:2:1). There were obtained 31.1 mg of (S)-1-[[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]methyl]dodecyl-N-isopropylmalonamate, m.p. 59°.

Workup

  1. filtrationwas filtered
  2. concentrationthe filtrate was concentrated
  3. customthe residue was chromatographed on silica gel with hexane/methylene chloride/ethyl acetate (2:2:1)

Sources & evidence

ORD record
ord-a026a2588d364b12848bea4b46211a5c
Source dataset
uspto-grants-1993_11
Patent number
US05260310

Reaction notes

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