HCID 22942079, compound → HCID 3011835, compound

HRID 362137Notes

Reaction equation

HRID 362137 reaction equation
[CH2:1]([S:8][CH2:9][C@H:10]([NH:16][C:17](=[O:80])[C@H:18]([CH2:76][CH:77]([CH3:79])[CH3:78])[NH:19][C:20](=[O:75])[C@H:21]([C:71]([CH3:74])([CH3:73])[CH3:72])[NH:22][C:23](=[O:70])[C@H:24]([CH2:62][C:63]1[CH:68]=[CH:67][CH:66]=[CH:65][C:64]=1[CH3:69])[NH:25][C:26](=[O:61])[C@H:27]([CH2:52][CH2:53][C:54](=[O:60])[O:55]C(C)(C)C)[NH:28][C:29](=[O:51])[C@H:30]([CH2:43][C:44](=[O:50])[O:45]C(C)(C)C)[NH:31][C:32](=[O:42])[CH2:33][CH2:34][C:35]([O:37]C(C)(C)C)=[O:36])[CH:11](OC)[O:12]C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>FC(F)(F)C(O)=O.ClCCl.O>[CH2:1]([S:8][CH2:9][C@H:10]([NH:16][C:17](=[O:80])[C@H:18]([CH2:76][CH:77]([CH3:78])[CH3:79])[NH:19][C:20](=[O:75])[C@H:21]([C:71]([CH3:72])([CH3:73])[CH3:74])[NH:22][C:23](=[O:70])[C@H:24]([CH2:62][C:63]1[CH:68]=[CH:67][CH:66]=[CH:65][C:64]=1[CH3:69])[NH:25][C:26](=[O:61])[C@H:27]([CH2:52][CH2:53][C:54](=[O:55])[OH:60])[NH:28][C:29](=[O:51])[C@H:30]([CH2:43][C:44](=[O:45])[OH:50])[NH:31][C:32](=[O:42])[CH2:33][CH2:34][C:35]([OH:37])=[O:36])[CH:11]=[O:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 22942079HCID 22942079, compound

Product 1

HCID 3011835HCID 3011835, compoundYield 88.1%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

56 mg (0.049 mmol) of N1-[2-(benzylthio)-1(R)-(dimethoxymethyl)ethyl]-N2-[N-[N-[N-[N-[3-(tert-butoxycarbonyl)propionyl]-O-tert-butyl-L-α-aspartyl]-O-tert-butyl-L-α-glutamyl]-2-methyl-L-phenylalanyl]-3-methyl-L-valyl]-L-leucinamide were dissolved in 10 ml of trifluoroacetic acid/dichloromethane (1:1) containing 3 drops of water and the solution was stirred for 90 minutes. The solution was evaporated to dryness under a vacuum and the residue was re-evaporated twice with toluene. The solid was triturated with 10 ml of diethyl ether to give 40 mg of 3-(benzylthio)-2(R)-[[N-[N-[N-[N-[N-(3-carboxypropionyl)-L-α-aspartyl]-L-α-glutamyl]-2-methyl-L-phenylalanyl]-3-methyl-L-valyl]-L-leucyl]amino]propionaldehyde as a white solid. MS: m/e 927.6 (M+H]+.

Workup

  1. customThe solution was evaporated to dryness under a vacuum
  2. customthe residue was re-evaporated twice with toluene
  3. customThe solid was triturated with 10 ml of diethyl ether

Sources & evidence

ORD record
ord-dd189ea35c134f5485f8424c6230baaf
Source dataset
uspto-grants-1999_02
Patent number
US05866684

Reaction notes

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