Anisole → HCID 12888645, compound

HRID 126792Notes

Reaction equation

HRID 126792 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:11]([NH:13][C@@H:14]([C:16]([NH:18][C@H:19]([C:27]([NH:29][C@H:30]([C:35]([OH:37])=[O:36])[CH2:31][CH2:32][S:33][CH3:34])=[O:28])[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:17])[CH3:15])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.C1(OC)C=CC=CC=1>C(O)(C(F)(F)F)=O>[NH2:1][C@H:2]([C:11]([NH:13][C@@H:14]([C:16]([NH:18][C@H:19]([C:27]([NH:29][C@H:30]([C:35]([OH:37])=[O:36])[CH2:31][CH2:32][S:33][CH3:34])=[O:28])[CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[O:17])[CH3:15])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 7519AnisoleHCID 12888631HCID 12888631, compound

Product 1

HCID 12888645HCID 12888645, compoundYield 69.2%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

In a fashion analogous to Step B of Example 3A, 1.1 g of Boc-Tyr-DAla-Phe-Met-OH was treated with 10% anisole in TFA and chromatographed on Amberlite XAD-2 to give 0.64 g (60%) of H-Tyr-DAla-Phe-Met-OH, m.p. 248°-249° C., [α]D25.5 =41.06° (c, 1.00 in 50% acetic acid).

Workup

  1. customchromatographed on Amberlite XAD-2

Sources & evidence

ORD record
ord-0f0e7fbb41eb43c5a03cd3f0cbc32531
Source dataset
uspto-grants-1981_03
Patent number
US04254024

Reaction notes

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