Sodium Hydroxide → Boc-Trp(Mtr)-OH

HRID 1649342Notes

Reaction equation

HRID 1649342 reaction equation
[NH:1]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C@H:2]([C:13]([O:15]CC1C=CC=CC=1)=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[CH3:30][O:31][C:32]1[CH:37]=[C:36]([CH3:38])[C:35]([S:39](Cl)(=[O:41])=[O:40])=[C:34]([CH3:43])[C:33]=1[CH3:44].[OH-].[Na+]>ClCCl.[Cl-].C([N+](C)(C)C)CCCCCCCCCCCCCCC>[NH:1]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C@H:2]([C:13]([OH:15])=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]([S:39]([C:35]2[C:34]([CH3:43])=[C:33]([CH3:44])[C:32]([O:31][CH3:30])=[CH:37][C:36]=2[CH3:38])(=[O:41])=[O:40])[CH:5]=1

Participants

6

Reactant 3

HCID 14798Sodium Hydroxide2×HCID 5627874-Methoxy-2,3,6-trimethylbenzenesulfonyl chlorideHCID 10318477Boc-trp-obzl

Product 1

HCID 131713226Boc-Trp(Mtr)-OH

Reagents, catalysts & solvents 2

HCID 8154Hexadecyltrimethylammonium chlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

In the same manner as Example 5, Boc-Trp-OBzl (1.97 g, 5 mM) was reacted with 4-methoxy-2,3,6-trimethylbenzene-sulfonyl chloride (1.87 g, 7.5 mM) in dichloromethane in the presence of sodium hydroxide (500 mg, 12.5 mM) and cetyltrimethylammonium chloride (16 mg, 0.05 mM). The reaction product was then hydrolyzed with an aqueous solution of sodium hydroxide to give Boc-Trp(Mtr)-OH. Yield 2.05 g (79.4%); m.p. 78°-80° C.; [α]D22 -24.8° (c=0.5, DMF).

Sources & evidence

ORD record
ord-0b5fe27e35054174b77b9a62de3e7338
Source dataset
uspto-grants-1983_11
Patent number
US04416820

Reaction notes

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