Boc-D-phenylalanine → HCID 22828222, compound

HRID 1633315Notes

Reaction equation

O.Cl.Cl.[NH2:4][C:5]1[N:13]=[CH:12][N:11]=[C:10]2[C:6]=1[N:7]=[CH:8][N:9]2[C@@H:14]1[O:19][C@H:18]([C:20]([OH:22])=[O:21])[C@@H:17]([NH:23][C:24](=[O:36])[C@H:25]([CH2:27][C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=2)[NH2:26])[C@H:15]1[OH:16].[C:37]([O:41][C:42]([NH:44][C@@H:45]([C:53](O)=[O:54])[CH2:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)=[O:43])([CH3:40])([CH3:39])[CH3:38]>>[NH2:4][C:5]1[N:13]=[CH:12][N:11]=[C:10]2[C:6]=1[N:7]=[CH:8][N:9]2[C@@H:14]1[O:19][C@H:18]([C:20]([OH:22])=[O:21])[C@@H:17]([NH:23][C:24](=[O:36])[C@H:25]([CH2:27][C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=2)[NH:26][C:53](=[O:54])[C@@H:45]([CH2:46][C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[NH:44][C:42]([O:41][C:37]([CH3:40])([CH3:38])[CH3:39])=[O:43])[C@H:15]1[OH:16]

Participants

Reactant 2

HCID 637610Boc-D-phenylalanine

HCID 70466244HCID 70466244, compound

Product 1

HCID 22828222HCID 22828222, compoundYield 89.6%

Procedure

1-(6-Amino-9H-purin-9-yl)-3-[N-(N-tert-butoxycarbonyl-β-phenyl-D-alanyl)-O-methyl-L-tyrosylamino]-1,3-dideoxy-β-D-ribofuranuronic acid (488 mg) was prepared by reacting 1-(6-amino-9H-purin-9-yl)-1,3-dideoxy-3-(O-methyl-L-tyrosylamino)-β-D-ribofuranuronic acid dihydrochloride monohydrate (424 mg) prepared in Example 4 with N-hydroxysuccinimide ester of N-tert-butoxycarbonyl-β-phenyl-D-alanine (290 mg) according to a similar manner to that of Example 5, mp. 164°-168° C. (dec.).

Sources & evidence

ORD record: ord-c0ed5be1f4f44a9da805e202c6bb95aa
Source dataset: uspto-grants-1984_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04479942

Reaction notes

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