Methanol → Sulfosalicylic Acid

HRID 1076077

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HRID 1076077 반응식
ClC1C=CC(P(C2C=CC(Cl)=CC=2)C2C=CC(Cl)=CC=2)=CC=1.C1(C)C=CC([S:29]([OH:32])(=[O:31])=[O:30])=CC=1.[H][H].[CH3:36][C@H:37]1[C:52]2[CH:53]=[CH:54][CH:55]=[C:56]([OH:57])[C:51]=2[C:50]([OH:58])=[C:49]2[C@@H:38]1[C@H:39]([OH:67])[C@@H:40]1[C@:46]([OH:59])([C:47]2=[O:48])[C:45]([OH:60])=[C:44]([C:61]([NH2:63])=[O:62])[C:42](=[O:43])[C@H:41]1[N:64]([CH3:66])[CH3:65].C[OH:69]>[Rh]>[CH3:36][C@H:37]1[C:52]2[CH:53]=[CH:54][CH:55]=[C:56]([OH:57])[C:51]=2[C:50]([OH:58])=[C:49]2[C@@H:38]1[C@H:39]([OH:67])[C@@H:40]1[C@:46]([OH:59])([C:47]2=[O:48])[C:45]([OH:60])=[C:44]([C:61]([NH2:63])=[O:62])[C:42](=[O:43])[C@H:41]1[N:64]([CH3:66])[CH3:65].[S:29]([C:53]1[CH:52]=[C:51]([C:50]([OH:58])=[O:69])[C:56]([OH:57])=[CH:55][CH:54]=1)([OH:32])(=[O:31])=[O:30]

참가 물질

8

반응물 5

HCID 887Methanol2회HCID 6101p-Toluenesulfonic acidHCID 70874Tris(4-chlorophenyl)phosphineHCID 546712034-(Dimethylamino)-1,5,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-3,4,4a,5,5a,6,12,12a-octahydrotetracene-2-carboximidic acidHCID 178418361HCID 178418361, 화합물

생성물 2

HCID 7322Sulfosalicylic AcidHCID 546712034-(Dimethylamino)-1,5,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-3,4,4a,5,5a,6,12,12a-octahydrotetracene-2-carboximidic acid

시약·촉매·용매 1

HCID 23948Rhodium촉매

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온도
62 °C

실험 절차

A Parr bottle is charged with 5% rhodium-on-carbon (2.88 gms., 50% wet material; 0.70 mM of rhodium), tri-(4-chlorophenyl)phosphine (0.76 gms., 2.1 mM) in 13 cc. methanol. The mixture is shaken for a half-hour at 62°C., under nitrogen atmosphere, at the end of which time a solution of 3.39 gms., 7.0 mM, of 6-deoxy-6-demethyl-6-methylene-5-hydroxytetracycline hydrochloride in 37 cc. of methanol, containing 7.0 mM of p-toluenesulfonic acid, is added. The bottle is then filled with hydrogen at 50 p.s.i. and shaken overnight at 75°C. for 18 hours. High pressure liquid chromatography of the reaction mixture indicates the presence of 80% α-6-deoxy-5-hydroxytetracycline and 1.5% 6β-epimer. α-6-deoxy-5-hydroxytetracycline may be isolated in 78% yield as the 5-sulfosalicyclic acid salt.

후처리

  1. additionis added
  2. stirringand shaken overnight at 75°C. for 18 hours

출처 및 근거

ORD 기록
ord-141ff0ebb7574873878f82ca2b74959c
출처 데이터셋
uspto-grants-1976_05
특허 번호
US03954862

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