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Glycine → N-carboxymethyl-1-(6-benzoylamino-9H-purin-9-yl)-1,3-dideoxy-3-(N-benzyloxycarbonyl-O-methyl-L-tyrosylamino)-beta-D-ribofuranuronamide

HRID 1633303
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HRID 1633303 반응식
[C:1]([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)[C@@H:22]([NH:28][C:29](=[O:51])[C@H:30]([CH2:42][C:43]2[CH:48]=[CH:47][C:46]([O:49][CH3:50])=[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:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:52][CH2:53][C:54]([OH:56])=[O:55].C(N(CC)CC)C>O1CCCC1.O>[C:54]([CH2:53][NH:52][C:25](=[O:27])[C@H:23]1[O:24][C@@H:19]([N:14]2[CH:13]=[N:12][C:11]3[C:15]2=[N:16][CH:17]=[N:18][C:10]=3[NH:9][C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C@H:20]([OH:21])[C@@H:22]1[NH:28][C:29](=[O:51])[C@H:30]([CH2:42][C:43]1[CH:44]=[CH:45][C:46]([O:49][CH3:50])=[CH:47][CH:48]=1)[NH:31][C:32]([O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:33])([OH:56])=[O:55]
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참가 물질

6

반응물 3

HCID 750GlycineHCID 8471TriethylamineHCID 704659181-(6-benzoylamino-9H-purin-9-yl)-1,3-dideoxy-3-(N-benzyloxycarbonyl-O-methyl-L-tyrosylamino)-beta-D-ribofuranuronic acid

생성물 1

HCID 70505043N-carboxymethyl-1-(6-benzoylamino-9H-purin-9-yl)-1,3-dideoxy-3-(N-benzyloxycarbonyl-O-methyl-L-tyrosylamino)-beta-D-ribofuranuronamide수율 81.1%

시약·촉매·용매 2

HCID 962
Water
용매
HCID 8028Tetrahydrofuran용매

실험 절차

A solution of N-hydroxysuccinimide ester of 1-(6-benzoylamino-9H-purin-9-yl)-1,3-dideoxy-3-(N-benzyloxycarbonyl-O-methyl-L-tyrosylamino)-β-D-ribofuranuronic acid (295 mg) prepared in Example 53 (1) in tetrahydrofuran was added to a solution of glycine (30 mg) and triethylamine (0.085 ml) in water (5 ml). The mixture was stirred for 20 hours at room temperature and concentrated under reduced pressure to remove tetrahydrofuran. The aqueous solution was acidified with 1N hydrochloric acid and extracted with a mixed solvent (chloroform/ethanol=1/1). The extract was dried and evaporated to dryness. The residue was triturated in diethyl ether to give N-carboxymethyl-1-(6-benzoylamino-9H-purin-9-yl)-1,3-dideoxy-3-(N-benzyloxycarbonyl-O-methyl-L-tyrosylamino)-β-D-ribofuranuronamide (244 mg), mp. 122°-130° C. (dec.).

후처리

  1. concentrationconcentrated under reduced pressure
  2. customto remove tetrahydrofuran
  3. extractionextracted with a mixed solvent (chloroform/ethanol=1/1)
  4. customThe extract was dried
  5. customevaporated to dryness
  6. customThe residue was triturated in diethyl ether

출처 및 근거

ORD 기록
ord-86f18a1f12cc42458dda7899c03441b3
출처 데이터셋
uspto-grants-1984_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04479942

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