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Diisopropylethylamine → N-((2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyl-tetrahydropyran-2-yloxy)-malonamic acid methyl ester

HRID 1038306
Notes
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Reaction equation

HRID 1038306 reaction equation
[CH3:1][O:2][C@@H:3]1[C@H:8]([O:9][CH3:10])[C@@H:7]([O:11][CH3:12])[C@H:6]([CH3:13])[O:5][C@H:4]1[O:14][NH2:15].CCN(C(C)C)C(C)C.Cl[CH:26]([C:31]([O-])=[O:32])[C:27]([O:29][CH3:30])=[O:28]>ClCCl>[CH3:30][O:29][C:27](=[O:28])[CH2:26][C:31]([NH:15][O:14][C@H:4]1[C@H:3]([O:2][CH3:1])[C@H:8]([O:9][CH3:10])[C@@H:7]([O:11][CH3:12])[C@H:6]([CH3:13])[O:5]1)=[O:32]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 57824423O-((2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyl-tetrahydropyran-2-yl)-hydroxylamineHCID 86762096Methyl chloromalonate

Product 1

HCID 86662685N-((2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyl-tetrahydropyran-2-yloxy)-malonamic acid methyl esterYield 58%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent
3×

Procedure

To a solution of O-((2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyl-tetrahydropyran-2-yl)-hydroxylamine (P-4; 157 mg, 0.71 mmol) in dichloromethane (CH2Cl2; 8 mL) was added DIEA (230 μL, 1.3 mmol) followed by a solution of methyl chloromalonate (137 mg, 1.0 mmol) dissolved in CH2Cl2 (2 mL). This mixture was allowed to stir at room temperature for 4 h. The mixture was then diluted with CH2Cl2 and washed with 1 N HCl. The aqueous fraction was extracted with CH2Cl2. The organic fractions were combined, dried with anhydrous Na2SO4 and evaporated at room temperature under vacuum. The resulting crude material was purified by silica gel chromatography (eluting with 75% EtOAc in Hexane). The title product (132 mg, 58%) was isolated as a colorless oil: 1H NMR (300 MHz, CDCl3) δ 10.00-9.38 (m, 1H), 5.06 (d, J=55.9 Hz, 1H), 4.02-2.92 (m, 18H), 1.39 (t, J=20.4 Hz, 3H); 13C NMR (101 MHz, CDCl3) δ 189.13, 101.59, 81.56, 77.24, 75.39, 69.66, 59.26, 57.89, 52.86, 39.75, 26.47, 17.85; ESIMS m/z 320 (M−H).

Workup

  1. washwashed with 1 N HCl
  2. extractionThe aqueous fraction was extracted with CH2Cl2
  3. dry with materialdried with anhydrous Na2SO4
  4. customevaporated at room temperature under vacuum
  5. customThe resulting crude material was purified by silica gel chromatography (eluting with 75% EtOAc in Hexane)

Sources & evidence

ORD record
ord-d7beb6359e294578a317ed5b83a5b851
Source dataset
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08551914B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes