Sodium Hydroxide → HCID 131713227, compound

HRID 1649343Notes

Reaction equation

HRID 1649343 reaction equation
C1C=CC(C[O:8][C:9]([C@@H:11]([NH:22][C:23]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:24])[CH2:12][C:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[NH:15][CH:14]=2)=[O:10])=CC=1.[CH3:33][O:34][C:35]1[CH:40]=[C:39]([CH3:41])[C:38]([S:42](Cl)(=[O:44])=[O:43])=[C:37]([CH3:46])[C:36]=1[CH3:47].[OH-].[Na+]>ClCCl>[NH:22]([C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24])[C@H:11]([C:9]([OH:10])=[O:8])[CH2:12][C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]([S:42]([C:38]2[C:37]([CH3:46])=[C:36]([CH3:47])[C:35]([O:34][CH3:33])=[CH:40][C:39]=2[CH3:41])(=[O:44])=[O:43])[CH:14]=1

Participants

5

Reactant 3

HCID 14798Sodium Hydroxide2×HCID 5627874-Methoxy-2,3,6-trimethylbenzenesulfonyl chlorideHCID 14102143N-[(Phenylmethoxy)carbonyl]-L-tryptophan phenylmethyl ester

Product 1

HCID 131713227HCID 131713227, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In the same manner as Example 5, Z-Trp-OBZl (15.0 g, 35 mM) and 4-methoxy-2,3,6-trimethylbenzenesulfonyl chloride were reacted in dichloromethane (500 ml) in the presence of sodium hydroxide (17.8 g, 0.44 M). The reaction product was then hydrolyzed with an aqueous solution of sodium hydroxide to give Z-Trp(Mtr)-OH. Yield 19.0 g (98.4%); m.p. 71°-74° C.; [α]D24 -41.6° (c=0.9, DMF).

Sources & evidence

ORD record
ord-f3eb644de84946f8b74a3aa59c14bf55
Source dataset
uspto-grants-1983_11
Patent number
US04416820

Reaction notes

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