Potassium Bromide → CID 71271091

HRID 335502노트

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HRID 335502 반응식
C(NC1S[C@H]2[O:12][C@H](CN3C=C(C4C=CC=CN=4)N=N3)[C@@H](O)[C@H](O)[C@H]2N=1)C.[CH2:27]([NH:29][C:30]1[S:31][C@H:32]2[O:38][C@H:37]([CH2:39][OH:40])[C@@H:36]([OH:41])[C@H:35]([OH:42])[C@H:33]2[N:34]=1)[CH3:28].CC1(C)N([O])C(C)(C)CCC1.[Br-].[K+].Cl[O-].[Na+]>C1COCC1>[CH2:27]([NH:29][C:30]1[S:31][C@H:32]2[O:38][C@H:37]([C:39]([OH:12])=[O:40])[C@@H:36]([OH:41])[C@H:35]([OH:42])[C@H:33]2[N:34]=1)[CH3:28]

참가 물질

7

반응물 5

HCID 253877Potassium BromideHCID 2724126Tempo2회HCID 23665760Sodium Hypochlorite2회HCID 24808478Thiamet G, >=98% (HPLC)HCID 178463442(3aR,5R,6S,7R,7aR)-2-(ethylamino)-5-[(4-pyridin-2-yltriazol-1-yl)methyl]-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d][1,3]thiazole-6,7-diol

생성물 1

HCID 71271091CID 71271091

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

The carboxylic acid intermediate of Schemes 1 to 3 was synthesized as follows: To a suspension of (3aR,5R,6S,7R,7aR)-2-(ethylamino)-5-(hydroxymethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol (23 g, 93 mmol) in 1:1 THF/aqueous NaHCO3 (1200 mL) was added TEMPO (3.2 g, 20 mmol) and potassium bromide (3.5 g, 30 mmol). The mixture was then cooled to 0° C. and a solution of sodium hypochlorite (190 mL, 9% active chlorine basis) was added, dropwise. After 1 h, additional amounts of sodium hypochlorite solution (95 mL) and TEMPO (1.6 g, 10 mmol) were added. After TLC analysis indicated the reaction was complete, the reaction solution was extracted with diethyl ether (2×250 mL). The aqueous layer was acidified with 5N HCl to pH 5-6, and then concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel using a gradient of methanol/dichloromethane (1% to 50%) to afford the title compound (23 g).

후처리

  1. extractionthe reaction solution was extracted with diethyl ether (2×250 mL)
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by flash chromatography on silica gel using a gradient of methanol/dichloromethane (1% to 50%)

출처 및 근거

ORD 기록
ord-6e20622b4a4e4d16abdaafa7ac6de133
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08884023B2

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