Sodium Chloride → HCID 10026366, compound

HRID 2294739Notes

Reaction equation

HRID 2294739 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH:12]([CH3:18])[CH:13](C)[C:14]([OH:16])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:20][O:21][C:22](=[O:34])[C@H:23]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=1)[NH2:24].[CH3:35]N(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.[Cl-].[Na+]>C(#N)C>[CH3:20][O:21][C:22](=[O:34])[C@H:23]([CH2:25][C:26]1[CH:27]=[CH:28][C:29]([O:32][CH3:33])=[CH:30][CH:31]=1)[NH:24][C:14](=[O:16])[CH2:13][C:12]([NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])([CH3:18])[CH3:35]

Participants

7

Reactant 5

HCID 5234Sodium ChlorideHCID 8471TriethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 14557400HCID 14557400, compoundHCID 69612215(S)-Methyl 2-amino-3-(4-methoxyphenyl)propanoate hydrochloride

Product 1

HCID 10026366HCID 10026366, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 1.12 g (4.47 mmol) of N-[(benzyloxy)carbonyl]-2,3-dimethyl-β-alanine (EPA 0230266), 1.1 g (4.47 mmol) of 3-(p-methoxyphenyl)-L-alanine methyl ester hydrochloride, 1.7 g (4.47 mmol) of HBTU and 1.25 ml (8.94 mmol) of triethylamine in 40 ml of acetonitrile is stirred at room temperature for 4 hours. After the addition of 50 ml of saturated sodium chloride solution the mixture is extracted 3 times with 50 ml of ethyl acetate each time. The combined organic phases are washed in sequence with 2N hydrochloric acid, water, 50% sodium hydrogen carbonate solution and water, dried over sodium sulphate and evaporated under reduced pressure. For purification, the residue is chromatographed on silica gel using a 95:5 mixture of methylene chloride and methanol as the eluent. N-[3-[1-(Benzyloxy)formamido]-3-methylbutyryl]-3-(p-methoxyphenyl)-L-alanine methyl ester is obtained as a colourless oil; MS: 443 (M+H)+.

Workup

  1. extractionis extracted 3 times with 50 ml of ethyl acetate each time
  2. washThe combined organic phases are washed in sequence with 2N hydrochloric acid, water, 50% sodium hydrogen carbonate solution and water
  3. dry with materialdried over sodium sulphate
  4. customevaporated under reduced pressure
  5. customFor purification
  6. customthe residue is chromatographed on silica gel using
  7. additiona 95:5 mixture of methylene chloride and methanol as the eluent

Sources & evidence

ORD record
ord-1a6cf864d3654add99271edae4558e29
Source dataset
uspto-grants-1997_11
Patent number
US05688946

Reaction notes

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