Diisopropylethylamine → tert-butyl (2S)-2-benzyloxycarbonylamino-3-(4-(2-methoxycarbonylethyl)benzoylamino)propionate

HRID 1394009Notes

Reaction equation

HRID 1394009 reaction equation
[CH3:1][O:2][C:3]([CH2:5][CH2:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=O)=[CH:9][CH:8]=1)=[O:4].[CH2:16]([O:23][C:24]([NH:26][C@@H:27]([CH2:35][NH2:36])[C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.F[B-](F)(F)F.C(C(=NOC(N(C)C)=[N+](C)C)C(OCC)=O)#N.C(N(C(C)C)CC)(C)C>CN(C=O)C>[CH2:16]([O:23][C:24]([NH:26][C@@H:27]([CH2:35][NH:36][C:11](=[O:13])[C:10]1[CH:9]=[CH:8][C:7]([CH2:6][CH2:5][C:3]([O:2][CH3:1])=[O:4])=[CH:15][CH:14]=1)[C:28]([O:30][C:31]([CH3:32])([CH3:33])[CH3:34])=[O:29])=[O:25])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 10803731(S)-tert-Butyl 3-amino-2-(((benzyloxy)carbonyl)amino)propanoateHCID 113102944-(3-Methoxy-3-oxopropyl)benzoic acid

Product 1

HCID 15512203tert-butyl (2S)-2-benzyloxycarbonylamino-3-(4-(2-methoxycarbonylethyl)benzoylamino)propionate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

354 mg (1.7 mmol) of 4-(2-methoxycarbonylethyl)benzoic acid (Example 3b) and 500 mg (1.7 mmol) of tert-butyl (2S)-2-benzyloxycarbonylamino-3-amino-propionate were dissolved in 3 ml of DMF and treated with 557 mg (1.7 mmol) of O-[[(cyano(ethoxycarbonyl)methylidene)amino]-1,1,3,3,-tetramethyluronium tetrafluoroborate (TOTU) and 204 mg (1.7 mmol) of diisopropylethylamine (DIPEA) and the solution was stirred at RT for 7 h. The solvent was evaporated in vacuo, the residue was dissolved in ethyl acetate (EA) and washed three times each with KHSO4 and NaHCO3 solution until neutral, the organic phase was separated off and dried, and the solvent was distilled off in vacuo. Yield: 770 mg (93%). MS: ES+, m/e=485.2 (M+H+, 100%)

Workup

  1. customThe solvent was evaporated in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate (EA)
  3. washwashed three times each with KHSO4 and NaHCO3 solution until neutral, the organic phase
  4. customwas separated off
  5. customdried
  6. distillationthe solvent was distilled off in vacuo

Sources & evidence

ORD record
ord-1b28375b2e554929b0f572a61354a398
Source dataset
uspto-grants-2008_03
Patent number
US07348333B2

Reaction notes

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