Diethyl Ether → HCID 70511552, compound

HRID 1262884Notes

Reaction equation

C([O:5][C:6]([N:8](C)[C@H:9]([C:22]([NH:24][C@@H:25]([C:30]([NH:32][CH2:33][CH2:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:31])[CH2:26][CH2:27][S:28][CH3:29])=[O:23])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17]C(C)(C)C)=[CH:13][CH:12]=1)=O)(C)(C)C.CCOCC.[ClH:48].O1CCOCC1>>[OH2:5].[ClH:48].[CH3:6][NH:8][C@H:9]([C:22]([NH:24][C@H:25]([C:30]([NH:32][CH2:33][CH2:34][CH2:35][C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)=[O:31])[CH2:26][CH2:27][S:28][CH3:29])=[O:23])[CH2:10][C:11]1[CH:12]=[CH:13][C:14]([OH:17])=[CH:15][CH:16]=1

Participants

Reactant 3

HCID 3283Diethyl Ether

HCID 204431481,4-Dioxane hydrochloride

HCID 70510866HCID 70510866, compound

Product 1

HCID 70511552HCID 70511552, compound

Procedure

A solution of [N-(tert-butyloxycarbonyl)-O-(tert-butyl)-N-methyl-L-tyrosyl]-N-(3-phenylpropyl)-D-methioninamide (1.9 g.) in hydrogen chloride-dioxane (3.9 N, 25 ml.) was stirred for 75 minutes at room temperature, then stripped of volatiles. Trituration of the residue with ether gave a white powder (1.308 g.), an aqueous solution of which was lyophilized, affording as an amorphous solid N-methyl-L-tyrosyl-N-(3-phenylpropyl)-L-methioninamide monohydrochloride hydrate (4:1) (1.260 g.; [α]D25 +68.0°, c=1, methanol), whose free base is the compound of Formula II wherein Q is Met, R1 is methyl, R2 and R5 are each hydrogen and R4 is (CH2)nY wherein n is 3 and Y is phenyl.

Sources & evidence

ORD record: ord-62d806c9446f45de999f039942a6390d
Source dataset: uspto-grants-1984_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04454120

Reaction notes

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