1,2-Dichloroethane → tert-Butyl 2-((2R,3S,4S)-3,4-dihydroxy-2-(4-methoxybenzyl)pyrrolidin-1-yl)-2-oxoethylcarbamate

HRID 1755451Notes

Reaction equation

HRID 1755451 reaction equation
[CH3:1][O:2][C:3]1[CH:16]=[CH:15][C:6]([CH2:7][C@@H:8]2[C@H:12]([OH:13])[C@@H:11]([OH:14])[CH2:10][NH:9]2)=[CH:5][CH:4]=1.[C:17]([O:21][C:22]([NH:24][CH2:25][C:26](O)=[O:27])=[O:23])([CH3:20])([CH3:19])[CH3:18].ON1C2N=CC=CC=2N=N1.CN1CCOCC1.C(Cl)CCl>C(Cl)Cl>[OH:13][C@@H:12]1[C@@H:11]([OH:14])[CH2:10][N:9]([C:26](=[O:27])[CH2:25][NH:24][C:22](=[O:23])[O:21][C:17]([CH3:18])([CH3:19])[CH3:20])[C@@H:8]1[CH2:7][C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:16][CH:15]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 78288N-(tert-butoxycarbonyl)glycineHCID 181649HOAtHCID 11790817Deacetylanisomycin

Product 1

HCID 86700100tert-Butyl 2-((2R,3S,4S)-3,4-dihydroxy-2-(4-methoxybenzyl)pyrrolidin-1-yl)-2-oxoethylcarbamateYield 96.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following the procedure as described in Example 24, except using the material from Example 39 (432 mg, 1.935 mmol), 2-(tert-butoxycarbonylamino)acetic acid (486.1 mg, 2.77 mmol), 1-hydroxy-7-azabenzotriazole (134.0 mg, 0.984 mmol), CH2Cl2 (20 mL), N-methylmorpholine (1.1 mL, 10.01 mmol), and EDC (560.5 mg, 2.92 mmol), 709.1 mg (96%) of the title compound is obtained as a white solid. Purification is done by BIOTAGE® Silica gel chromatography on a 25 g Thompson Single Step silica cartridge using a linear gradient from 100% CH2Cl2 to 100% EtOAc/Hexanes over 12 column volumes. LC/MS (Condition A): ret. T=3.07 min, (M+Na) 403.20.

Sources & evidence

ORD record
ord-7dc374a0265e4776be9adb57b81e76f0
Source dataset
uspto-grants-2015_10
Patent number
US09169295B2

Reaction notes

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