L-Iditol, 1,2,5,6-tetradeoxy-2,5-bis(((1,1-dimethylethoxy)carbonyl)amino)-1,6-diphenyl- → (2S,3R,4R,5S)-2,5-diamino-3,4-dihydroxy-1,6-diphenylhexane

HRID 1078126Notes

Reaction equation

C(OC([NH:8][C@H:9]([C@@H:17]([OH:36])[C@H:18]([OH:35])[C@@H:19]([NH:27]C(OC(C)(C)C)=O)[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=O)(C)(C)C>Cl>[NH2:8][C@H:9]([C@@H:17]([OH:36])[C@H:18]([OH:35])[C@@H:19]([NH2:27])[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

Conditions

Temperature: 90 °C

Procedure

(2S,3R,4R,5S)-2,5-Di-(N-((t-butyloxy)carbonyl)amino)-3,4-dihydroxy-1,6-diphenylhexane (2.7 g, 5.4 mmol) was treated with 200 ml of 6N aqueous hydrochloric acid and heated to 90° C. until the solid had completely dissolved (30 min). The resulting solution was cooled, concentrated in vacuo, treated with saturated brine and 3N aqueous NaOH, extracted with chloroform, dried over Na2SO4, and concentrated in vacuo. Silica gel chromatography using 3% methanol/2% isopropylamine in chloroform provided the pure desired compound (Rf 0.40, 5% methanol/2% isopropylamine in chloroform) as a white solid, m.p. 86°-89° C. 1H NMR (CDCl3) δ2.72 (dd, J=14, 9 Hz, 2H), 2.92 (dd, J=14, 6 Hz, 2H), 3.03 (dd, J=9, 5 Hz, 2H), 3.69 (s, 2H), 7.15-7.35 (m, 10H). Mass spectrum: (M+H)+ =301.

Workup

dissolutionhad completely dissolved (30 min)
temperatureThe resulting solution was cooled
concentrationconcentrated in vacuo
additiontreated with saturated brine and 3N aqueous NaOH
extractionextracted with chloroform
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-3b726bea2d6a4bcbb4e2fc3be7045383
Source dataset: uspto-grants-1996_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05545750

Reaction notes

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