Reaction #11675

ord-f6b32ea6655540abb07919434d96aeb2

Reaction equation

COC(=O)CN1C(=O)[C@H](NC(=O)c2cc3cc(Cl)ccc3[nH]2)Cc2ccccc21
(R)-1-carbomethoxymethyl-3-(5-chloroindole-2-carbonylamino)-3,4-dihydrocarbostyril
CC(C)(C)OC(=O)N[C@@H]1Cc2ccccc2NC1=O
(R)-3-t-butyloxycarbonylamino-3,4-dihydrocarbostyril
O=C(N[C@@H]1Cc2ccccc2NC1=O)c1cc2cc(Cl)ccc2[nH]1
(S)-3-t-butyloxycarbonylamino-3,4-dihydrocarbostyril
O=C(N[C@@H]1Cc2ccccc2NC1=O)c1cc2cc(Cl)ccc2[nH]1
(R)-3-(5-chloroindole-2-carbonylamino)-3,4-dihydrocarbostyril
→
COC(=O)CN1C(=O)[C@@H](NC(=O)c2cc3cc(Cl)ccc3[nH]2)Cc2ccccc21
title compound
COC(=O)CN1C(=O)[C@@H](NC(=O)c2cc3cc(Cl)ccc3[nH]2)Cc2ccccc21
(S)-1-carbomethoxymethyl-3-(5-chloroindole-2-carbonylamino)-3,4-dihydrocarbostyril

Reactants

COC(=O)CN1C(=O)[C@H](NC(=O)c2cc3cc(Cl)ccc3[nH]2)Cc2ccccc21
(R)-1-carbomethoxymethyl-3-(5-chloroindole-2-carbonylamino)-3,4-dihydrocarbostyril
CC(C)(C)OC(=O)N[C@@H]1Cc2ccccc2NC1=O
(R)-3-t-butyloxycarbonylamino-3,4-dihydrocarbostyril
O=C(N[C@@H]1Cc2ccccc2NC1=O)c1cc2cc(Cl)ccc2[nH]1
(S)-3-t-butyloxycarbonylamino-3,4-dihydrocarbostyril
O=C(N[C@@H]1Cc2ccccc2NC1=O)c1cc2cc(Cl)ccc2[nH]1
(R)-3-(5-chloroindole-2-carbonylamino)-3,4-dihydrocarbostyril

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

The title compound was prepared from (S)-3-t-butyloxycarbonylamino-3,4-dihydrocarbostyril (prepared in Example 5) by the procedures described for the preparation of (R)-1-carbomethoxymethyl-3-(5-chloroindole-2-carbonylamino)-3,4-dihydrocarbostyril (Example 7) from (R)-3-t-butyloxycarbonylamino-3,4-dihydrocarbostyril. HPLC/MS [M+H]+, 412.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07098235B2uspto-grants-2006_08