1,2-Dichloroethane → HCID 21034201, compound

HRID 272278Notes

Reaction equation

HRID 272278 reaction equation
[CH2:1]([N:4]([CH2:13][CH2:14][CH3:15])[C:5]([CH2:7][CH2:8][CH2:9][C:10]([OH:12])=O)=[O:6])[CH:2]=[CH2:3].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.FC(F)(F)C([O-])=O.[CH2:37]([O:40][C:41]1[CH:42]=[C:43]([CH:70]=[C:71]([F:73])[CH:72]=1)[CH2:44][CH:45]([NH3+:69])[CH:46]([OH:68])[CH2:47][N:48]([C:58]([O:60][CH2:61][C:62]1[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=1)=[O:59])[CH2:49][C:50]1[CH:55]=[CH:54][CH:53]=[C:52]([CH2:56][CH3:57])[CH:51]=1)[CH:38]=[CH2:39]>C(Cl)Cl.CCOC(C)=O>[CH2:61]([O:60][C:58](=[O:59])[N:48]([CH2:47][CH:46]([OH:68])[CH:45]([NH:69][C:10](=[O:12])[CH2:9][CH2:8][CH2:7][C:5](=[O:6])[N:4]([CH2:1][CH:2]=[CH2:3])[CH2:13][CH2:14][CH3:15])[CH2:44][C:43]1[CH:70]=[C:71]([F:73])[CH:72]=[C:41]([O:40][CH2:37][CH:38]=[CH2:39])[CH:42]=1)[CH2:49][C:50]1[CH:55]=[CH:54][CH:53]=[C:52]([CH2:56][CH3:57])[CH:51]=1)[C:62]1[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 22046581HCID 22046581, compoundHCID 22046606HCID 22046606, compound

Product 1

HCID 21034201HCID 21034201, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of [4-(3-Allyloxy-5-fluoro-phenyl)-3-tert-butoxycarbonylamino-2-hydroxy-butyl]-(3-ethyl-benzyl)-carbamic acid benzyl ester (1.84 g, 3.03 mmol) in 20% TFA/DCM (30 mL) is prepared and stirred for 1 hour. The reaction mixture is concentrated in vacuo yielding a white solid (2.12 g). Peptide coupling is performed by preparing a solution of 4-(allyl-propyl-carbamoyl)-butyric acid (0.060 g, 2.82 mmol) in CH2Cl2 to which is added EDC (0.74 g, 3.84 mmol) and HOBT (0.52 g, 3.84 mmol) under N2, with stirring. To this solution is added a solution of TEA (1.43 mL, 10.24 mmol), 1-(3-Allyloxy-5-fluoro-benzyl)-3-[benzyloxycarbonyl-(3-ethyl-benzyl)-amino]-2-hydroxy-propyl-ammonium trifluoro-acetate (1.59 g, 2.56 mmol) dissolved in CH2Cl2 (15 mL). Upon complete reaction the mixture is diluted with EtOAc, washed with NaHCO3 and then 1N HCl. The mixture is then neutralized with NaHCO3, and then 0.5N NaOH, treated with activated charcoal, dried with MgSO4, filtered, concentrated in vacuo, yielding a yellow oil. Purification is achieved via flash chromatography using 75% EtOAc/Hexanes. Calculated mass for C41H52FN3O6+H1: 702.3918. Accurate mass found for C41H52FN3O6+H1: 702.3916.

Workup

  1. customUpon complete reaction the mixture
  2. washwashed with NaHCO3
  3. addition0.5N NaOH, treated with activated charcoal
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customyielding a yellow oil
  8. customPurification

Sources & evidence

ORD record
ord-c3a878ec7d07484dabb9ad9bd81d737d
Source dataset
uspto-grants-2008_11
Patent number
US07456163B2

Reaction notes

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