Dichloromethane → HCID 22942064, compound

HRID 362155Notes

Reaction equation

HRID 362155 reaction equation
C([O:5][C:6]([NH:8][C@H:9]([C:18]([NH:20][C@H:21]([C:31]([NH:33][C@H:34]([C:43]([NH:45][C@H:46]([C:51]([NH:53][C@H:54]([C:59]([NH:61][CH:62]([B:67]1[O:71]C(C)(C)C(C)(C)[O:68]1)[CH2:63][CH2:64][CH2:65][F:66])=[O:60])[CH2:55][CH:56]([CH3:58])[CH3:57])=[O:52])[C:47]([CH3:50])([CH3:49])[CH3:48])=[O:44])[CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[CH3:42])=[O:32])[CH2:22][CH2:23][C:24](=[O:30])[O:25]C(C)(C)C)=[O:19])[CH2:10][C:11](=[O:17])[O:12]C(C)(C)C)=O)(C)(C)C.ClCCl>FC(F)(F)C(O)=O.O.C1(C)C=CC=CC=1>[F:66][CH2:65][CH2:64][CH2:63][CH:62]([B:67]([OH:68])[OH:71])[NH:61][C:59](=[O:60])[C@H:54]([CH2:55][CH:56]([CH3:57])[CH3:58])[NH:53][C:51](=[O:52])[C@H:46]([C:47]([CH3:48])([CH3:50])[CH3:49])[NH:45][C:43](=[O:44])[C@H:34]([CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[CH3:42])[NH:33][C:31](=[O:32])[C@H:21]([CH2:22][CH2:23][C:24](=[O:30])[OH:25])[NH:20][C:18](=[O:19])[C@H:9]([CH2:10][C:11](=[O:17])[OH:12])[NH:8][C:6](=[O:5])[CH2:9][CH2:10][C:11]([OH:17])=[O:12]

Participants

6

Reactant 2

HCID 6344DichloromethaneHCID 22942110HCID 22942110, compound

Product 1

HCID 22942064HCID 22942064, compoundYield 121.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

200 mg (0.18 mmol) of N2-[N-[N-[N-[N-(tert-butoxycarbonyl)-O-tert-butyl-L-α-aspartyl]-O-tert-butyl-L-α-glutamyl]-2-methyl-L-phenylalanyl]-3-methyl-L-valyl]-N1-[4-fluoro-1(RS)-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)butyl]-L-leucinamide were dissolved in 4.75 ml of trifluoroacetic acid and 0.25 ml of water. 2 ml of dichloromethane were added and the solution was stirred at room temperature for 3 hours. The solution was diluted with toluene and evaporated. The residue was triturated with diethyl ether and the resulting solid was filtered off and dried to give 95 mg of 4-fluoro-1(RS)-[[N-[N-[N-[N-[N-(3-carboxypropionyl)-L-α-aspartyl]-L-α-glutamyl]-2-methyl-L-phenylalanyl]-3-methyl-L-valyl]-L-leucyl]amino]butylboronic acid; MS: m/e 849.4 [M+H-H2O]+.

Workup

  1. customevaporated
  2. customThe residue was triturated with diethyl ether
  3. filtrationthe resulting solid was filtered off
  4. customdried

Sources & evidence

ORD record
ord-056747104bdb4522a500b788d2d80f07
Source dataset
uspto-grants-1999_02
Patent number
US05866684

Reaction notes

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