Dichloromethane → HCID 53701063, compound

HRID 487851Notes

Reaction equation

HRID 487851 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:17]([OH:19])=O)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(OC(N[C@H](C(O)=O)CC1C=CC=CC=1)=O)(C)(C)C.[N+:39]([C:42]1[CH:62]=[CH:61][C:45]([CH2:46][NH:47][C:48](=[O:60])[C@H:49]([CH3:59])[NH:50][C:51](=[O:58])[C@H:52]([CH2:54][CH:55]([CH3:57])[CH3:56])[NH2:53])=[CH:44][CH:43]=1)([O-:41])=[O:40].C(Cl)Cl>C(OCC)(=O)C>[N+:39]([C:42]1[CH:62]=[CH:61][C:45]([CH2:46][NH:47][C:48](=[O:60])[C@H:49]([CH3:59])[NH:50][C:51](=[O:58])[C@H:52]([CH2:54][CH:55]([CH3:56])[CH3:57])[NH:53][C:17](=[O:19])[C@H:9]([CH2:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])=[CH:44][CH:43]=1)([O-:41])=[O:40]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-HCID 637610Boc-D-phenylalanineHCID 53856319HCID 53856319, compound

Product 1

HCID 53701063HCID 53701063, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Parallel syntheses for the D-isomer (R1 =H, R2 =benzyl) and L-isomer (R1 =benzyl, R2 =H) were performed. The following procedure was used for each. The procedure of Example 2, Section B was followed, using t-butoxycarbonyl-D-phenylalanine for one isomer and t-butoxycarbonyl-L-phenylalanine for the other, and using L-leucyl-L-alanine 4-nitrobenzylamide of the formula ##STR28## instead of (-)N-(L-2-hydroxy-4-methylpentanoyl)-L-alanine 4-nitrobenzyl amide. The reaction was carried out on a 2.0 mmol scale, using methylene chloride (10 mL) instead of dimethylformamide as the solvent. After the extractions, the crude product was purified by silica gel chromatography, eluting with 7:3 methylene chloride:ethyl acetate to afford the products as white solids (D-isomer: 0.83 g, 1.42 mmol, 71% yield; L-isomer: 0.77 g, 1.3 mmol, 62% yield). Verification of the structures was as follows:

Workup

  1. extractionAfter the extractions
  2. customthe crude product was purified by silica gel chromatography
  3. washeluting with 7:3 methylene chloride

Sources & evidence

ORD record
ord-7fa03597f06b41b48f90717ad5062c32
Source dataset
uspto-grants-1994_03
Patent number
US05298409

Reaction notes

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