Butylamine → 1-(6-Amino-9H-purin-9-yl)-3-(N-benzyloxycarbonyl-O-benzyl-L-tyrosylamino)-1,3-dideoxy-beta-D-ribofuranuronic acid

HRID 1633294Notes

Reaction equation

C([NH:9][C:10]1[N:18]=[CH:17][N:16]=[C:15]2[C:11]=1[N:12]=[CH:13][N:14]2[C@@H:19]1[O:24][C@H:23]([C:25]([OH:27])=[O:26])[C@@H:22]([NH:28][C:29](=[O:57])[C@H:30]([CH2:42][C:43]2[CH:48]=[CH:47][C:46]([O:49][CH2:50][C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)=[CH:45][CH:44]=2)[NH:31][C:32]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[O:33])[C@H:20]1[OH:21])(=O)C1C=CC=CC=1.C(N)CCC>>[NH2:9][C:10]1[N:18]=[CH:17][N:16]=[C:15]2[C:11]=1[N:12]=[CH:13][N:14]2[C@@H:19]1[O:24][C@H:23]([C:25]([OH:27])=[O:26])[C@@H:22]([NH:28][C:29](=[O:57])[C@H:30]([CH2:42][C:43]2[CH:44]=[CH:45][C:46]([O:49][CH2:50][C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)=[CH:47][CH:48]=2)[NH:31][C:32]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[O:33])[C@H:20]1[OH:21]

Participants

Reactant 2

HCID 8007Butylamine

HCID 704652771-(6-Benzoylamino-9H-purin-9-yl)-3-(N-benzyloxycarbonyl-O-benzyl-L-tyrosylamino)-1,3-dideoxy-beta-D-ribofuranuronic acid

Product 1

HCID 705037061-(6-Amino-9H-purin-9-yl)-3-(N-benzyloxycarbonyl-O-benzyl-L-tyrosylamino)-1,3-dideoxy-beta-D-ribofuranuronic acidYield 79.1%

Procedure

1-(6-Amino-9H-purin-9-yl)-3-(N-benzyloxycarbonyl-O-benzyl-L-tyrosylamino)-1,3-dideoxy-β-D-ribofuranuronic acid (130 mg) was prepared by reacting 1-(6-benzoylamino-9H-purin-9-yl)-3-(N-benzyloxycarbonyl-O-benzyl-L-tyrosylamino)-1,3-dideoxy-β-D-ribofuranuronic acid (190 mg) prepared in Example 12 with n-butylamine (1.5 ml) according to a similar manner to that of Example 23, mp. 173°-176° C. (dec.).

Sources & evidence

ORD record: ord-6d0c2458c5b54648baba0d1f5cb5aabb
Source dataset: uspto-grants-1984_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04479942

Reaction notes

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