Reaction #59396

ord-0d28a80794ba46daab20f682468c283a

Reaction equation

O=C(N[C@@H]1Cc2ccccc2NC1=O)c1cc2cc(Cl)ccc2[nH]1
(R)-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
→
O=C(N[C@H]1Cc2ccccc2NC1=O)c1cc2cc(Cl)ccc2[nH]1
title compound
O=C(N[C@H]1Cc2ccccc2NC1=O)c1cc2cc(Cl)ccc2[nH]1
(S)-3-(5-chloroindole-2-carbonylamino)-3,4-dihydrocarbostyril

Reactants

O=C(N[C@@H]1Cc2ccccc2NC1=O)c1cc2cc(Cl)ccc2[nH]1
(R)-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)-3-(5-chloroindole-2-carbonylamino)-3,4-dihydrocarbostyril (Example 5) from (R)-3-t-butyloxycarbonylamino-3,4-dihydrocarbostyril. HPLC/MS [M+H]+, 340; [M+Na]+, 362.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07425550B2uspto-grants-2008_09