Triethylamine → HCID 88402809, compound

HRID 257113Notes

Reaction equation

HRID 257113 reaction equation
[C:1]([CH2:4][CH:5]([O:26][CH3:27])[O:6][C@@H:7]([CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:8][C@H:9]([OH:20])[C@H:10]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[C:11]([OH:13])=O)(=[O:3])[NH2:2].C(N(CC)CC)C.CN(C(ON1N=N[C:45]2[CH:46]=[CH:47][CH:48]=[CH:49][C:44]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl.C(#N)C>[CH2:14]([C@@H:10]1[C:11](=[O:13])[O:20][C@H:9]1[CH2:8][C@@H:7]([O:6][CH:5]([O:26][CH3:27])[CH2:4][C:1]([NH2:2])=[O:3])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:48][CH2:49][CH2:44][CH2:45][CH2:46][CH3:47])[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 131718244HCID 131718244, compound

Product 1

HCID 88402809HCID 88402809, compoundYield 42.2%

Reagents, catalysts & solvents 1

HCID 21877088Acetonitrile methylene chlorideSolvent

Procedure

A solution of 42.5 mg of (2S,3S,5S)-5-[(R/S)-2-carbamoyl-1-methoxyethoxy]-2-hexyl-3-hydroxydecanoic acid (Example Kd)) in 10 ml of methylene chloride/acetonitrile (1:1) was treated with 1 g of molecular sieve (4 Å), 0.1 ml of triethylamine and 50 mg of HBTU. After stirring the reaction mixture was filtered and concentrated and the residue was partitioned between hexane and methanol/water (1:1); the aqueous methanolic phase was extracted with hexane, the hexane phase was dried and concentrated; the residue was subsequently chromatographed on silica gel with 5 percent methanol in methylene chloride. There were obtained 21 mg of (R/S)-3-[[(S)-1-[[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]methyl]dodecyl]oxy]-3-methoxypropionamide (epimers 3:1), m.p. 54°.

Workup

  1. filtrationwas filtered
  2. concentrationconcentrated
  3. customthe residue was partitioned between hexane and methanol/water (1:1)
  4. extractionthe aqueous methanolic phase was extracted with hexane
  5. dry with materialthe hexane phase was dried
  6. concentrationconcentrated
  7. customthe residue was subsequently chromatographed on silica gel with 5 percent methanol in methylene chloride

Sources & evidence

ORD record
ord-c5f77b1e8a1a46d194c9acc8e6f842fd
Source dataset
uspto-grants-1993_11
Patent number
US05260310

Reaction notes

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