Sodium Hydroxide → BocPro-MeDTrpOH

HRID 2418626Notes

Reaction equation

[N:1]1([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:24][CH2:23][CH2:22][C@H:2]1[C:3]([N:5]([CH3:21])[C@@H:6]([C:17]([O:19]C)=[O:18])[CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][CH:9]=1)=[O:4].[OH-].[Na+]>>[N:1]1([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:24][CH2:23][CH2:22][C@H:2]1[C:3]([N:5]([CH3:21])[C@@H:6]([C:17]([OH:19])=[O:18])[CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][CH:9]=1)=[O:4]

Participants

Reactant 2

HCID 14798Sodium Hydroxide

HCID 131713818BocPro-MeDTrpOMe

Product 1

HCID 131713819BocPro-MeDTrpOHYield 77%

Procedure

Condensation of BocProOH (4.63 g.) and MeDTrpOMe (5.00 g.) by the mixed anhydride method using diphenylphosphinyl chloride gave BocPro-MeDTrpOMe in 69% yield. Demethylation of BocPro-MeDTrpOMe (6.33 g.) using aqueous sodium hydroxide gave BocPro-MeDTrpOH in 77% yield. Condensation of BocPro-MeDTrpOH (3.60 g.) and HPheOBz (3.70 g.) using dicyclohexylcarbodiimide and N-hydroxysuccinimide gave BocPro-MeDTrp-PheOBz in 83% yield. Debenzylation of BocPro-MeDTrp-PheOBz (4.60 g.) by hydrogenation with palladium catalyst gave BocPro-MeDTrp-PheOH in 100% yield.

Sources & evidence

ORD record: ord-e9c74f35fa354fb6b4d2e114b7d2c5a7
Source dataset: uspto-grants-1984_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04472305

Reaction notes

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