Hydrochloric Acid → HCID 20637706, compound

HRID 429905Notes

Reaction equation

HRID 429905 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:24](O)=[O:25])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]([CH2:21][CH2:22][Cl:23])[CH2:18][CH2:19][Cl:20])=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1([C:32]2[CH:33]=[C:34]([CH:45]=[CH:46][CH:47]=2)[CH2:35][C@@H:36]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[NH2:37])CCCC1.Cl.CN1CCOCC1.C[CH2:57][CH2:58][CH2:59][CH2:60][CH3:61]>CCOC(C)=O.C(Cl)CCl.C(Cl)Cl>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:24]([N:37]([CH:57]1[CH2:58][CH2:59][CH2:60][CH2:61]1)[C@H:36]([C:38]([O:40][C:41]([CH3:42])([CH3:43])[CH3:44])=[O:39])[CH2:35][C:34]1[CH:33]=[CH:32][CH:47]=[CH:46][CH:45]=1)=[O:25])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]([CH2:18][CH2:19][Cl:20])[CH2:21][CH2:22][Cl:23])=[CH:13][CH:12]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 8058HexaneHCID 10883993HCID 10883993, compoundHCID 20706042HCID 20706042, compound

Product 1

HCID 20637706HCID 20637706, compoundYield 46%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A 50 mL round bottomed flask equipped with a magnetic stirrer was charged with 96 mg of N-((tert-butoxy)carbonyl)-4-(bis(2-chloroethyl)amino)-L-phenylalanine 77 mg of tert-butyl 3-cyclopentyl-L-phenylalaninate.HCl, and 10 mL of CH2Cl2. The solution was cooled to 0° C. and treated with 48 mg of EDC (Aldrich) followed by 0.026 mL of N-methylmorpholine. The reaction mixture was stirred at 0° C. for 20 min, allowed to warm to RT, and stirred for an additional 2 h. Analysis of the solution by tlc (SiO2, 7:3 hexane:EtOAc) indicated a major new component at Rf=0.54 and four minor components at Rf=0.4, 0.37, 0.16 and 0.0. The solution was concentrated in vacuo to dryness and the residue was subjected to flash chromatography on 50 g of silica gel to afford 73 mg (46%) of tert-butyl N-((tert-butoxy)carbonyl)-4-(bis(2-chloroethyl)amino)-L-phenylalanyl-(3-cyclopenty)-L-phenylalaninate as a thick semi-solid.

Workup

  1. customA 50 mL round bottomed flask equipped with a magnetic stirrer
  2. temperatureto warm to RT
  3. stirringstirred for an additional 2 h
  4. concentrationThe solution was concentrated in vacuo to dryness

Sources & evidence

ORD record
ord-ebe17c0921c3493f81a0f8ab32ad4316
Source dataset
uspto-grants-2001_11
Patent number
US06319702B1

Reaction notes

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