Water → HCID 86737819, compound

HRID 1680809Notes

Reaction equation

[CH3:1][O:2][C@H:3]1[C@H:10]([CH3:11])[O:9][C@@H:6]([O:7]C)[CH2:5][C@H:4]1[NH:12][C:13](=[O:18])[C:14]([F:17])([F:16])[F:15].O>C(O)(=O)C>[CH3:1][O:2][C@H:3]1[C@H:10]([CH3:11])[O:9][C@@H:6]([OH:7])[CH2:5][C@H:4]1[NH:12][C:13](=[O:18])[C:14]([F:17])([F:16])[F:15]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 1.76 g; 6.5 mmol of compound VI in 35 ml of acetic acid there were added 140 ml of water. The solution was then heated at 100° C. for 1 hour. The solvent was then evaporated off and the residue was recrystallized from carbon tetrachloride to give 1.64 g (yield 98%) of 4-O-methyl-2,3,6-trideoxy-3-trifluoroacetamido-α-L-ribohexopyranose (VII); m.p. 113°-115° C.; [α]D23° =-61.5° (c=0.5 in CHCl3); mass spectrum; m/e 257 (M+). The p.m.r. spectrum showed absoption at: 1.27 (d, CH3 --C--5), 2.96 (dd, J=9.5 and 4.0 Hz, C--4--H), 3.44 (s, CH3O), 4.00 (dq, J=6.5 and 9.5 Hz, C--5--H), 4,69 (m, C--3--H) and 5.32 (broad s, WH =6.0 Hz, C--1--H).

Workup

customThe solvent was then evaporated off
customthe residue was recrystallized from carbon tetrachloride

Sources & evidence

ORD record: ord-55d16e7da8094022a9a74fce2c44ebe5
Source dataset: uspto-grants-1981_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04276289

Reaction notes

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