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 2424994Notes

Reaction equation

HRID 2424994 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-93b1c17a8be847e194671e017abd670f
Source dataset
uspto-grants-2011_06
Patent number
US07964601B2

Reaction notes

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