Ammonia → HCID 54047045, compound

HRID 129075Notes

Reaction equation

HRID 129075 reaction equation
N.[CH2:2]([C@@H:8]1[C:11](=[O:12])[O:10][C@H:9]1[CH2:13][C@@H:14]([O:26][CH2:27][CH2:28][C:29]([OH:31])=O)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].C[N:33](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(#N)C>[C:29]([CH2:28][CH2:27][O:26][C@@H:14]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:13][C@@H:9]1[O:10][C:11](=[O:12])[C@H:8]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])(=[O:31])[NH2:33]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 54166902HCID 54166902, compound

Product 1

HCID 54047045HCID 54047045, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Ammonia gas was blown into a solution of 40 mg of 3-[[(S)-1-[[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]methyl]dodecyl]oxy]propionic acid (Example L) in 2.5 ml of acetonitrile until the solution is saturated and subsequently 50 mg of HBTU were added. Then, the mixture was filtered and evaporated and the residue was chromatographed on silica gel with 5 percent methanol in methylene chloride. There were obtained 32.5 mg of (3S,4S)-4-[(S)-2-(2-carbamoylethoxy)tridecyl]-3-hexyl-2-oxetanone, m.p. 35°.

Workup

  1. filtrationThen, the mixture was filtered
  2. customevaporated
  3. customthe residue was chromatographed on silica gel with 5 percent methanol in methylene chloride

Sources & evidence

ORD record
ord-cc54a1b48634473cb204ba665648f9bc
Source dataset
uspto-grants-1995_11
Patent number
US05466708

Reaction notes

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