Dimethyl Sulfoxide → HCID 57013824, compound

HRID 1872453Notes

Reaction equation

C([O:3][C:4]([C@@H:6]1[C@@H:11]2[C@H:7]1[CH2:8][C@@H:9]([OH:25])[C@@:10]2([N:22]=[N+:23]=[N-:24])[C:12]([O:14]CC1C=CC=CC=1)=[O:13])=[O:5])C.O[Li].O.CS(C)=O>C1COCC1.O>[N:22]([C@@:10]1([C:12]([OH:14])=[O:13])[C@H:9]([OH:25])[CH2:8][C@@H:7]2[C@H:11]1[C@H:6]2[C:4]([OH:5])=[O:3])=[N+:23]=[N-:24]

Participants

Conditions

Temperature: 23 °C

Procedure

To a solution of (1S,2R,3R,5R,6S)-2-azido-3-hydroxy-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester (VII) (845 mg, 2.45 mmol) in THF (21 mL) and H2O (6 mL) was added LiOH.H2O (411 mg, 9.8 mmol) and the mixture was stirred at 23° C. for 18 h. The benzyl alcohol was extracted with ether, the aqueous layer acidified with 1 M KHSO4 -sol., saturated with solid NaCl, extracted with EtOAc (4×50 mL) and dried over MgSO4. After removal of the solvent under vacuum crude (1S,2R,3R,5R,6S)-2-azido-3-hydroxy-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid (XI) (581 mg, quant.) was obtained as white solid, sufficiently pure for further transformations. 1H-NMR (250 MHz, DMSO) □1.75 (1H, t, J=3.5 Hz), 1.84 (1H, m), 1.92-2.07 (2H, m), 2.15 (1H, dd, J=12.5, 7 Hz), 3.87 (1H, btJ=7 Hz); MS[ISN] 226 [(M-H)-]; mp 124-128° C.; □D20 -61.48° (c=0.90, H2O).

Workup

extractionThe benzyl alcohol was extracted with ether
extraction, saturated with solid NaCl, extracted with EtOAc (4×50 mL)
dry with materialdried over MgSO4
customAfter removal of the solvent under vacuum crude (1S,2R,3R,5R,6S)-2-azido-3-hydroxy-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid (XI) (581 mg, quant.)
customwas obtained as white solid, sufficiently pure for further transformations

Sources & evidence

ORD record: ord-f27b399bd6d3481983e48a750483e34c
Source dataset: uspto-grants-2000_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06107342

Reaction notes

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