D-3-(2-Naphthyl)alanine → n-{2-[2(s)-(3-Guanidino-propyl)-5(r)-methyl-4-(2-naphthalen-2-yl-acetyl)-piperazin-1-yl]-1 (r)-naphthalen-2-ylmethyl-2-oxo-ethyl}-acetamide

HRID 272653Notes

Reaction equation

HRID 272653 reaction equation
[NH2:1][C@H:2]([CH2:32][C:33]1[CH:42]=[CH:41][C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:34]=1)[C:3]([N:5]1[CH2:10][C@@H:9]([CH3:11])[N:8]([C:12](=[O:24])[CH2:13][C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=2)[CH2:7][C@@H:6]1[CH2:25][CH2:26][CH2:27][NH:28][C:29]([NH2:31])=[NH:30])=[O:4].N[C@@H:44]([C:56](O)=[O:57])CC1C=C2C(C=CC=C2)=CC=1>>[NH:28]([CH2:27][CH2:26][CH2:25][C@H:6]1[CH2:7][N:8]([C:12](=[O:24])[CH2:13][C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=2)[C@H:9]([CH3:11])[CH2:10][N:5]1[C:3](=[O:4])[C@H:2]([NH:1][C:56](=[O:57])[CH3:44])[CH2:32][C:33]1[CH:42]=[CH:41][C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:34]=1)[C:29]([NH2:31])=[NH:30]

Participants

3

Reactant 2

HCID 2733661D-3-(2-Naphthyl)alanineHCID 178461576n-{3-[1-(2(r)-Amino-3-naphthalen-2-yl-propionyl)-5(r)-methyl-4-(2-naphthalen-2-yl-acetyl)-piperazin-2(s)-yl]-propyl}-guanidine

Product 1

HCID 178475061n-{2-[2(s)-(3-Guanidino-propyl)-5(r)-methyl-4-(2-naphthalen-2-yl-acetyl)-piperazin-1-yl]-1 (r)-naphthalen-2-ylmethyl-2-oxo-ethyl}-acetamide

Procedure

The following compound was synthesized by the method of Scheme 6. The compound of Example 38 was treated by the method of Example 36 to introduce an acetyl group at the amino group of the D-2-Nal residue. It was tested as described above with the results shown. The mass was analyzed as 607.7 (M+H).

Workup

  1. customThe following compound was synthesized by the method of Scheme 6

Sources & evidence

ORD record
ord-b35af4103a02471c9772ee65d86092c9
Source dataset
uspto-grants-2008_11
Patent number
US07456184B2

Reaction notes

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