(Diethylamino)sulfur trifluoride → HCID 59013482, compound

HRID 1716977Notes

Reaction equation

HRID 1716977 reaction equation
[CH2:1]([O:8][C@@H:9]1[C@@H:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@H:13]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@@H:12]([CH2:31][O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[O:11][C@:10]21[C:47]1[C:42](=[CH:43][C:44]([Cl:57])=[C:45]([CH2:48][C:49]3[CH:54]=[CH:53][C:52]([CH2:55][CH3:56])=[CH:51][CH:50]=3)[CH:46]=1)[CH:41](O)[CH2:40]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(S(F)(F)[F:65])CC>ClCCl>[CH2:1]([O:8][C@@H:9]1[C@@H:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@H:13]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@@H:12]([CH2:31][O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[O:11][C@:10]21[C:47]1[C:42](=[CH:43][C:44]([Cl:57])=[C:45]([CH2:48][C:49]3[CH:54]=[CH:53][C:52]([CH2:55][CH3:56])=[CH:51][CH:50]=3)[CH:46]=1)[CH:41]([F:65])[CH2:40]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 59013481HCID 59013481, compound

Product 1

HCID 59013482HCID 59013482, compoundYield 87.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a −78° C. solution of (1S,3′R,4′S,5′R,6′R)-3′,4′,5′-tris(benzyloxy)-6′-(benzyloxymethyl)-5-chloro-6-(4-ethylbenzyl)-2,3,3′,4′,5′,6′-hexahydrospiro[indene-1,2′-pyran]-3-ol (40 mg, 0.05 mmol) in dry dichloromethane (2.0 mL) was added dropwise a solution of DAST reagent (0.014 mL, 0.1 mmol, 95%) in 0.5 mL of dry dichloromethane. The reaction mixture was stirred for 2 h at −78° C. and quenched by addition of 1 mL of saturated aqueous NaHCO3 solution when TLC showed the reaction was complete. The organic layer was separated and the aqueous layer was extracted 2× with CH2Cl2 (10 mL). The combined organic layers were washed 2× with NaHCO3 (10 mL), 3× with brine (10 mL) prior to drying over anhydrous Na2SO4. Concentrated under reduced pressure and purification of the crude product by prepared TLC provided 35 mg of the pure product.

Workup

  1. customquenched by addition of 1 mL of saturated aqueous NaHCO3 solution when TLC
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted 2× with CH2Cl2 (10 mL)
  4. washThe combined organic layers were washed 2× with NaHCO3 (10 mL), 3× with brine (10 mL)
  5. dry with materialto drying over anhydrous Na2SO4
  6. concentrationConcentrated under reduced pressure and purification of the crude product
  7. customby prepared TLC

Sources & evidence

ORD record
ord-9be26208249647138e0532aa97e9f207
Source dataset
uspto-grants-2010_09
Patent number
US07803778B2

Reaction notes

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