Diisopropylcarbodiimide → Z-N-Me-Phg-Tyr(3-tBu)-NH2

HRID 1383719Notes

Reaction equation

HRID 1383719 reaction equation
[C:1]([N:11]([CH3:22])[C@H:12]([C:19]([OH:21])=O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[NH2:23][C@H:24]([C:37]([NH2:39])=[O:38])[CH2:25][C:26]1[CH:31]=[CH:30][C:29]([OH:32])=[C:28]([C:33]([CH3:36])([CH3:35])[CH3:34])[CH:27]=1.C1C=CC2N(O)N=NC=2C=1.CC(C)N=C=NC(C)C>CN(C=O)C.C(OCC)(=O)C>[C:1]([N:11]([CH3:22])[C@H:12]([C:19]([NH:23][C@H:24]([C:37]([NH2:39])=[O:38])[CH2:25][C:26]1[CH:31]=[CH:30][C:29]([OH:32])=[C:28]([C:33]([CH3:36])([CH3:34])[CH3:35])[CH:27]=1)=[O:21])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2]

Participants

7

Reactant 4

HCID 12734DiisopropylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 11289554N-Cbz-(S)-a-(methylamino)-benzeneacetic acidHCID 131722727Tyr(3-tBu)-NH2

Product 1

HCID 131722734Z-N-Me-Phg-Tyr(3-tBu)-NH2

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3.28 g (11.0 mmol) of Z-N-Me-Phg-OH, 2.16 g (9.17 mmol) of Tyr(3-tBu)-NH2 and 1.40 g (9.17 mmol) of HOBT in 60 ml of DMF, 1.42 ml (9.17 mmol) of DIC was added dropwise under cooling with ice and the mixture was stirred for 4 hours under cooling with ice. The reaction mixture was diluted with ethyl acetate and washed with saturated brine. The organic layer was dried with anhydrous sodium sulfate and concentrated under reduced pressure; the resulting residue was subjected to silica gel column chromatography (eluting solvent consisting of methylene chloride, methanol and aqueous ammonia at a ratio of 100:5:1) to give Z-N-Me-Phg-Tyr(3-tBu)-NH2 in the amount of 4.03 g (85%).

Workup

  1. temperatureunder cooling with ice
  2. temperatureunder cooling with ice
  3. washwashed with saturated brine
  4. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. washeluting solvent

Sources & evidence

ORD record
ord-987864f9f7024b809e1555e1106de3bd
Source dataset
uspto-grants-2001_07
Patent number
US06255285B1

Reaction notes

Loading…