1,2-Dichloroethane → HCID 53943221, compound

HRID 636005Notes

Reaction equation

[CH3:1][CH:2]([CH3:13])[CH2:3][C@H:4]([C@H:8]([OH:12])[CH2:9][CH2:10][CH3:11])[C:5]([OH:7])=O.[O:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH:15]1[O:20][NH2:21].C(Cl)CCl>ClCCl.CCOC(C)=O>[O:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH:15]1[O:20][NH:21][C:5](=[O:7])[C@H:4]([CH2:3][CH:2]([CH3:1])[CH3:13])[C@H:8]([OH:12])[CH2:9][CH2:10][CH3:11]

Participants

Conditions

Temperature: 25 °C

Procedure

To a stirred solution of (2R,3R)-2-(2-methyl-1-propyl)-3-hydroxyhexanoic acid (6.0 g, 32.3 mmol) in 33 mL of dichloromethane at 0° C. is added 2-tetrahydropyranyloxyamine (7.70 g, 65.8 mmol) followed by EDC (7.50 g, 39.4 mmol). The reaction mixture is allowed to warm to 25° C., stirred 12 h, then diluted with 100 mL of EtOAc and washed successively with 50 mL each of water, 1 M aqueous sodium bisulfate solution, saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride. The combined organic layers are dried over sodium sulfate and filtered, and the solvents are removed under reduced pressure. Purification by flash chromatography on silica gel eluting with 10% EtOAc-hexanes affords 9.0 g (97%) of (2R,3R)-2-(2-methyl-1-propyl)-3-hydroxyhexanoic acid 2-tetrahydropyranyloxyamide as a gum.

Workup

washwashed successively with 50 mL each of water, 1 M aqueous sodium bisulfate solution, saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride
dry with materialThe combined organic layers are dried over sodium sulfate
filtrationfiltered
customthe solvents are removed under reduced pressure
customPurification by flash chromatography on silica gel eluting with 10% EtOAc-hexanes

Sources & evidence

ORD record: ord-f344d46d32514b8c9343b1e26f34ef09
Source dataset: uspto-grants-2001_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06191150B1

Reaction notes

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