Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate → HCID 21970279, compound

HRID 1872789Notes

Reaction equation

HRID 1872789 reaction equation
[OH:1][C@@H:2]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:3][C:4]([NH2:6])=[O:5].[CH2:20]([O:27][C:28]([CH2:30][CH2:31][CH2:32][C@H:33]([NH:37][C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[C:34](O)=[O:35])=[O:29])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>ClCCl.CN(C)C1C=CN=CC=1>[CH2:20]([O:27][C:28]([CH2:30][CH2:31][CH2:32][C@H:33]([NH:37][C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[C:34]([O:1][C@@H:2]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:3][C:4]([NH2:6])=[O:5])=[O:35])=[O:29])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

6

Reactant 3

HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 109590796-(Benzyloxy)-N-(tert-butoxycarbonyl)-6-oxo-L-norleucineHCID 54536665HCID 54536665, compound

Product 1

HCID 21970279HCID 21970279, compoundYield 50.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a suspended solution of (S)-3-hydroxyhexadecanamide (3.45 g) and (S)-5-benzyloxycarbonyl-2-(tertiarybutoxycarbonylamino)pentanoic acid (4.50 g) in dichloromethane (150 ml) were added benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate (5.66 g) and 4-dimethylaminopyridine (3.13 g). The mixture was stirred overnight. The precipitates were filtered off, and the filtrate was concentrated under reduced pressure. The residue was dissolved in ethyl acetate (150 ml) and washed with 1N hydrochloric acid (100 ml×3), water (100 ml), saturated sodium bicarbonate (100 ml×2), and brine (100 ml). Then, the solution was dried over magnesium sulfate, and concentrated under reduced pressure. The residue was chromatographed on a silica gel column to give (3S)-3-[(2S)-5-benzyloxycarbonyl-2-(tertiarybutoxycarbonylamino)-pentanoyl]oxyhexadecanamide (3.85 g).

Workup

  1. filtrationThe precipitates were filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate (150 ml)
  4. washwashed with 1N hydrochloric acid (100 ml×3), water (100 ml), saturated sodium bicarbonate (100 ml×2), and brine (100 ml)
  5. dry with materialThen, the solution was dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was chromatographed on a silica gel column

Sources & evidence

ORD record
ord-1896ab93deb24f02b3bce3f8753b4dec
Source dataset
uspto-grants-2000_08
Patent number
US06110933

Reaction notes

Loading…