Benzyltrimethylammonium methoxide → HCID 178457138, compound

HRID 1611804Notes

Reaction equation

HRID 1611804 reaction equation
[CH:1]([NH:4][C@H:5]([C:12]([OH:14])=O)[CH2:6][C:7]1[N:11]=[CH:10][NH:9][CH:8]=1)([CH3:3])[CH3:2].[NH2:15][C@@H:16]([CH2:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[CH:27][CH:26]=1)[C:17]([NH:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18].C[O-].C([N+](C)(C)C)C1C=CC=CC=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.C(OCC)C>[CH2:32]([O:31][C:28]1[CH:29]=[CH:30][C:25]([CH2:24][CH:16]([NH:15][C:12](=[O:14])[CH:5]([NH:4][CH:1]([CH3:2])[CH3:3])[CH2:6][C:7]2[N:11]=[CH:10][NH:9][CH:8]=2)[C:17](=[O:18])[NH:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[CH:26][CH:27]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

7

Reactant 4

HCID 8504Benzyltrimethylammonium methoxideHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 15517727(S)-2-amino-3-(4-benzyloxy-phenyl)-N-tert-butyl-propionamideHCID 178457506HCID 178457506, compound

Product 1

HCID 178457138HCID 178457138, compoundYield 18.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
3 °C

Procedure

A solution of N-isopropylhistidine (302 mg, 1.53 mmol), (S)-2-amino-3-(4-benzyloxy-phenyl)-N-tert-butyl-propionamide (500 mg, 1.32 mmol), and benzyltrimethylammonium methoxide (40% solution in methanol, 2.1 mL, 3.36 mmol) in 10 mL dry DMF was cooled to 3° C. Then, HBTU (581 mg, 1.53 mmol) was added and the resulting mixture stirred at 3° C. for 60 minutes, warmed to 25° C., diluted with 35 mL diethyl ether, and washed with saturated aqueous sodium bicarbonate solution (35 mL) as well as with brine (35 mL), dried over anhydrous sodium sulfate, and concentrated at reduced pressure. The residue thus obtained was further purified twice by silica gel chromatography using 10% methanol in chloroform as eluant, to give 122 mg (13%) of the title compound as the dihydrochloride salt.

Workup

  1. temperaturewarmed to 25° C.
  2. washwashed with saturated aqueous sodium bicarbonate solution (35 mL) as well as with brine (35 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated at reduced pressure
  5. customThe residue thus obtained
  6. customwas further purified twice by silica gel chromatography

Sources & evidence

ORD record
ord-4390baddfdb144a19b0baa3503e7163d
Source dataset
uspto-grants-2006_01
Patent number
US06989448B2

Reaction notes

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