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Diisopropylethylamine → HCID 86591129, compound

HRID 276725
Notes
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Reaction equation

HRID 276725 reaction equation
[NH2:1][CH:2]([CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([O:16][CH3:17])=[O:15])[CH:9]=1)[C:3]#[N:4].[CH3:18][C:19]1[CH:20]=[C:21]([CH:43]=[CH:44][CH:45]=1)[CH2:22][C@@H:23]([C:40](O)=[O:41])[NH:24][C:25](=[O:39])[CH:26]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(N(C(C)C)CC)(C)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1>C(Cl)Cl>[CH3:17][O:16][C:14]([C:10]1[CH:9]=[C:8]([CH:13]=[CH:12][CH:11]=1)[O:7][CH2:6][CH2:5][CH:2]([NH:1][C:40](=[O:41])[C@H:23]([CH2:22][C:21]1[CH:43]=[CH:44][CH:45]=[C:19]([CH3:18])[CH:20]=1)[NH:24][C:25](=[O:39])[CH:26]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[C:3]#[N:4])=[O:15]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2724699PyBOP2×HCID 10933398HCID 10933398, compoundHCID 53706240HCID 53706240, compound

Product 1

HCID 86591129HCID 86591129, compound

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

To a solution of 2-amino-4-[3-(methoxycarbonyl)-phenoxy]-butyronitrile (0.5 g, 2.13 mmol), 3-methyl-N-(2,2-diphenylacetyl)-L-phenylalanine (see example 1, 0.80 g, 2.13 mmol) and diisopropylethylamine (1.1 mL, 6.39 mmol) in CH2Cl2 (15 mL) is added benzotriazol-1-yloxy-tris-(pyrrolidino)-phosphonium hexafluorophosphate (PyBop, 1.22 g, 2.34 mmol) in one portion. After stirring 1.5 hour, an additional portion of PyBop (0.61 g, 1.2 mmol) is added, and the solution is stirred overnight. The reaction mixture is washed with 1 N HCl (50 mL), saturated aqueous NaHCO3 (1×50 mL), water (1×50 mL) and brine (1×50 mL), dried over MgSO4, and evaporated. The residue is chromatographed (silica, 50% EtOAc/hexane) to yield N-[3-(3-(methoxycarbonyl)-phenoxy)-1-cyanopropyl]-3-methyl-Nα-(2,2-diphenylacetyl)-L-phenylalaninamide as a white solid, m.p. 152-153° C.

Workup

  1. stirringthe solution is stirred overnight
  2. washThe reaction mixture is washed with 1 N HCl (50 mL), saturated aqueous NaHCO3 (1×50 mL), water (1×50 mL) and brine (1×50 mL)
  3. dry with materialdried over MgSO4
  4. customevaporated
  5. customThe residue is chromatographed (silica, 50% EtOAc/hexane)

Sources & evidence

ORD record
ord-7ce5edde2f2d433e807a00b9ad6f0bb3
Source dataset
uspto-grants-2002_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06353017B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes