Water → Z-N-Me-Val-N-Me-Tyr(3-tBu)-OMe

HRID 1383740Notes

Reaction equation

HRID 1383740 reaction equation
[C:1]([N:11]([CH3:19])[C@H:12]([C:16]([OH:18])=O)[CH:13]([CH3:15])[CH3:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[NH:20]([CH3:38])[C@H:21]([C:34]([O:36][CH3:37])=[O:35])[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([OH:29])=[C:25]([C:30]([CH3:33])([CH3:32])[CH3:31])[CH:24]=1.C1C=CC2N(O)N=NC=2C=1.O>CN(C=O)C.CC(C)N=C=NC(C)C.CCOCC>[C:1]([N:11]([CH3:19])[C@H:12]([C:16]([N:20]([CH3:38])[C@H:21]([C:34]([O:36][CH3:37])=[O:35])[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([OH:29])=[C:25]([C:30]([CH3:33])([CH3:31])[CH3:32])[CH:24]=1)=[O:18])[CH:13]([CH3:14])[CH3:15])([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2]

Participants

8

Reactant 4

HCID 962WaterHCID 757711-HydroxybenzotriazoleHCID 7016371N-Methyl-N-[(phenylmethoxy)carbonyl]-L-valineHCID 131722749N-Me-Tyr(3-tBu)-OMe

Product 1

HCID 131722748Z-N-Me-Val-N-Me-Tyr(3-tBu)-OMe

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 12734DiisopropylcarbodiimideSolvent

Procedure

To a solution of 3.25 g of Z-N-Me-Val-OH, 2.2 g of N-Me-Tyr(3-tBu)-OMe and 1.88 g of HOBT in DMF (30 ml), DIC (1.9 ml) was added under cooling with ice and the mixture was stirred at room temperature for 23 hours. Water was added to the reaction mixture and extraction was effected with ether. The extract was washed with saturated brine and the organic layer was dried with sodium sulfate. After distilling off the solvent under reduced pressure, the resulting residue was subjected to silica gel column chromatography (eluting solvent consisting of chloroform, methanol and aqueous ammonia at a ratio of 100:10:1) to give Z-N-Me-Val-N-Me-Tyr(3-tBu)-OMe in the amount of 1.96 g (47%).

Workup

  1. temperatureunder cooling with ice
  2. washThe extract was washed with saturated brine
  3. dry with materialthe organic layer was dried with sodium sulfate
  4. distillationAfter distilling off the solvent under reduced pressure
  5. washeluting solvent

Sources & evidence

ORD record
ord-d7def5f59e1748acb24adfc0f6389594
Source dataset
uspto-grants-2001_07
Patent number
US06255285B1

Reaction notes

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