Benzenepropanoic acid → HCID 86748804, compound

HRID 1648118Notes

Reaction equation

HRID 1648118 reaction equation
C(OC([NH:8][C@H:9]([C:13]([NH:15][C@H:16]([C:18]([NH:20][CH:21]1[CH:25]([O:26]CC2C=CC=CC=2)[O:24][C:23](=[O:34])[CH2:22]1)=[O:19])[CH3:17])=[O:14])[CH:10]([CH3:12])[CH3:11])=O)(C)(C)C.[C:35]1([CH2:41][CH2:42][C:43]([OH:45])=O)[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.OC1C2N=NNC=2C=CC=1.CN1CCOCC1.C(N=C=NCCCN(C)C)C>FC(F)(F)C(O)=O.C(OCC)(=O)C.CN(C)C=O>[C:35]1([CH2:41][CH2:42][C:43]([NH:8][C@H:9]([C:13]([NH:15][C@H:16]([C:18]([NH:20][CH:21]([CH:25]=[O:26])[CH2:22][C:23]([OH:34])=[O:24])=[O:19])[CH3:17])=[O:14])[CH:10]([CH3:11])[CH3:12])=[O:45])[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Participants

9

Reactant 5

HCID 107Benzenepropanoic acidHCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 70043135HCID 70043135, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 86748804HCID 86748804, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6422Trifluoroacetic acidSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-(Tert-butoxycarbonyl-valinyl-alaninyl)-4-amino-5-benzyloxy-2-oxotetrahydrofuran (590.4 mg) was dissolved in 15 mL of trifluoroacetic acid, aged for 15 minutes, and concentrated. The residue was dissolved in methanol, diluted with toluene and concentrated to give a colorless solid. To 201.9 mg of this solid was added 3-phenylpropionic acid (123 mg, 0. 8216 mmol), hydroxybenzotriazole (111 mg, 0.8216 mmol), dimethyl formamide (3 mL), and 4-methylmorpholine (45 μl, 0.4108 mmol). Ethyl dimethylaminopropyl carbodiimide (83 mg, 0.4313 mmol) was added and the mixture stirred for 16 hours at ambient temperature. The mixture was diluted with ethyl acetate and washed three times with 2N hydrochloric acid, and twice with dilute sodium bicarbonate. The organics were dried over sodium sulfate, filtered and concentrated to give the title compound as a mixture of two diastereomers: 1H NMR (400 MHz, CD3OD) δ7.4-7.1 (m, 10H, Ar--H), 5.63 (d, 0.5H, J=5.03 Hz, CHOBn), 5.45 (d, 0.5H, J=1.20 Hz, CHOBn), 4.95-4.6 (m, 2.5H, CH2Ph, CHN), 4.4-4.2 (m, 1.5H, CHN), 4.08 (d, 0.5H, J=7.38 Hz, CHN), 4.03 (d, 0.5H, J=7.15 Hz, CH N), 3.03 (dd, 0.5H, J=8.11, 18.3 Hz, CHHCO2), 2.89 (dd, 2H, J=5.49, 8.79 Hz, CH2CON), 2.76 (dd, 0.5H, J=8.76, 17.38 Hz, CHHCO2), 2.7-2.4 (m, 3H, CHHCO2, CH2CH2Ph), 1.98 (m, 1H, CH(CH3)2), 1.31 (d, 1.5H, CHCH3), 1.25 (d, 1.5H, CHCH), 0.87 (m, 6H, CH(CH3)2. ##STR36## N-(3-Phenylpropionyl-valinyl-alaninyl)-3-amino-4-oxobutanoic acid

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in methanol
  3. additiondiluted with toluene
  4. concentrationconcentrated
  5. customto give a colorless solid
  6. washwashed three times with 2N hydrochloric acid
  7. dry with materialThe organics were dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-f5ee278d25fa4bba8a20614f60ee6600
Source dataset
uspto-grants-1995_07
Patent number
US05434248

Reaction notes

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