Triethylamine → (R)-alpha-[(2-Benzyloxycarbonylamino-2-methyl-1-oxopropyl)amino]-1H-indole-3-propanoic acid, allyl ester

HRID 1919

Reaction equation

HRID 1919 reaction equation
[CH2:1]([O:4][C:5](=[O:18])[C@@H:6]([CH2:8][C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[NH:11][CH:10]=1)[NH2:7])[CH:2]=[CH2:3].C(N(CC)CC)C.[CH2:26]([O:33][C:34]([NH:36][C:37]([CH3:42])([C:39](O)=[O:40])[CH3:38])=[O:35])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=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>C(Cl)Cl.C(OCC)(=O)C>[CH2:26]([O:33][C:34]([NH:36][C:37]([CH3:42])([CH3:38])[C:39]([NH:7][C@H:6]([CH2:8][C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[NH:11][CH:10]=1)[C:5]([O:4][CH2:1][CH:2]=[CH2:3])=[O:18])=[O:40])=[O:35])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 294936N-((Benzyloxy)carbonyl)-2-methylalanineHCID 7006689D-Tryptophan allyl ester

Product 1

HCID 86752262(R)-alpha-[(2-Benzyloxycarbonylamino-2-methyl-1-oxopropyl)amino]-1H-indole-3-propanoic acid, allyl esterYield 84.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

D-Tryptophan allyl ester (250 mg; 0.822 mmol), triethylamine (230 μl; 1.650 mmol) and N-benzyloxycarbonyl-α-methylalanine (167.9 mg; 0.826 mmol) were dissolved in dry methylene chloride (5 ml) and BOP (363.7 mg; 0.822 mmol) added. The reaction mixture was stirred at room temperature for 16 h and then the reaction quenched with saturated brine (5 ml). The methylene chloride layer was separated, dried with magnesium sulfate and filtered then the volatiles removed under reduced pressure to leave a dark brown oil. Chromatography of this oil on silica gel using ethyl acetate and hexanes 2:1 v/v afforded 322 mg (84.5%) of the desired product. FAB-MS:- calculated for C26H29N3O5 463.2; found 464.5 (M+1).

Workup

  1. customthe reaction quenched with saturated brine (5 ml)
  2. customThe methylene chloride layer was separated
  3. dry with materialdried with magnesium sulfate
  4. filtrationfiltered
  5. customthe volatiles removed under reduced pressure
  6. customto leave a dark brown oil

Sources & evidence

ORD record
ord-275c3bd4a2eb43f196b2a4707e52cd1b
Source dataset
uspto-grants-1998_03
Patent number
US05726319

Linked notes

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