Tetrahydrofuran → HCID 69544082, compound

HRID 891671Notes

Reaction equation

HRID 891671 reaction equation
C([CH:5]1[CH:8](OC2C=CC=CC=2)[N:7]([C:16]2[S:17][CH:18]=[C:19]([C:21](=[O:62])[NH:22][CH:23]([CH2:43][O:44][Si](C(C)(C)C)(C3C=CC=CC=3)C3C=CC=CC=3)[CH2:24][O:25][Si](C(C)(C)C)(C3C=CC=CC=3)C3C=CC=CC=3)[N:20]=2)[CH:6]1OC1C=CC=CC=1)(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[O:88]1CCCC1>>[OH:88][CH:5]1[CH2:6][N:7]([C:16]2[S:17][CH:18]=[C:19]([C:21](=[O:62])[NH:22][CH:23]([CH2:24][OH:25])[CH2:43][OH:44])[N:20]=2)[CH2:8]1

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 2724141Tetrabutylammonium FluorideHCID 131725362HCID 131725362, compound

Product 1

HCID 69544082HCID 69544082, compoundYield 100%

Procedure

To a solution of 3-t-butyldiphenyloxy-1-{4-[2-(t-butyldiphenylsilyloxy)-1-(t-butyldiphenylsilyloxymethyl)ethylcarbamoyl]-1,3-thiazol-2-yl}azetidine (3.19 g, 3.23 mmol) (obtained as described in Reference Example 39(3)) in anhydrous tetrahydrofuran (160 ml) was added a solution of 1.0M tetra-n-butylammonium fluoride in tetrahydrofuran (11.6 ml, 11.6 mmol) in an ice bath. The mixture was stirred in the ice bath for 2 hours. After checking the completion of the reaction, the reaction mixture was concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using ethyl acetate:methanol (9:1→8:2) as the eluant to afford 3-hydroxy-1-{4-[2-hydroxy-1-(hydroxymethyl)-ethylcarbamoyl]-1,3-thiazol-2-yl}azetidine (1.21 g, yield 100%) as a white solid.

Workup

  1. customthe completion of the reaction
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-c4bbe5d38cf9424d8a1e404fb32aa2c3
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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