(R)-2-((tert-Butoxycarbonyl)amino)-3-(2,4-dichlorophenyl)propanoic acid → HCID 68432630, compound

HRID 899163Notes

Reaction equation

HRID 899163 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][CH2:12][N:13]1[CH2:18][CH2:17][NH:16][CH:15]([CH2:19][CH2:20][CH2:21][N:22]2[C:30](=[O:31])[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:23]2=[O:32])[CH2:14]1.[CH3:33][C:34]([O:37][C:38]([NH:40][C@@H:41]([C:51](O)=[O:52])[CH2:42][C:43]1[CH:48]=[CH:47][C:46]([Cl:49])=[CH:45][C:44]=1[Cl:50])=[O:39])([CH3:36])[CH3:35]>C1C=NC2N(O)N=NC=2C=1.CN(C=O)C>[C:34]([O:37][C:38](=[O:39])[NH:40][CH:41]([CH2:42][C:43]1[CH:48]=[CH:47][C:46]([Cl:49])=[CH:45][C:44]=1[Cl:50])[C:51]([N:16]1[CH2:17][CH2:18][N:13]([CH2:12][CH2:11][C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:1]=2)[CH2:14][CH:15]1[CH2:19][CH2:20][CH2:21][N:22]1[C:30](=[O:31])[C:29]2=[CH:28][CH:27]=[CH:26][CH:25]=[C:24]2[C:23]1=[O:32])=[O:52])([CH3:36])([CH3:33])[CH3:35]

Participants

5

Reactant 2

HCID 7010031(R)-2-((tert-Butoxycarbonyl)amino)-3-(2,4-dichlorophenyl)propanoic acidHCID 68431420HCID 68431420, compound

Product 1

HCID 68432630HCID 68432630, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 181649HOAtSolvent

Procedure

To a mixture of 6-6 (42 mg, 0.10 mmol) and BOC-D-2,4-dichlorophenylalanine (66 mg, 2 eq) in 0.4 mL of 0.5 M HOAt in DMF and 0.5 mL of anhydrous DMF was added diisopropylcarboimide (24 mg, 2 equivalents). The reaction mixture was stirred at room temperature overnight. The solvent was evaporated in vacuo and the crude was purified with column chromatography (eluted with hexanes, ethyl acetate 1:2). The purified product, {1-(2,4-Dichloro-benzyl)-2-[2-[3-phthalimido-propyl]-4-(2-naphthalen-2-yl-ethyl)-piperazin-1-yl]-2-oxo-ethyl}-carbamic acid tert-butyl ester (6-7) was obtained as white solid, 30 mg (40%).

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe crude was purified with column chromatography (eluted with hexanes, ethyl acetate 1:2)

Sources & evidence

ORD record
ord-8f311a6e274f49968ba27618d8059855
Source dataset
uspto-grants-2008_04
Patent number
US07354923B2

Reaction notes

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