HCID 131724098, compound → HCID 87222126, compound

HRID 2119769Notes

Reaction equation

HRID 2119769 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([C:19]([OH:21])=[O:20])[CH2:10][O:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH3:18])=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(Cl)(Cl)Cl>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:19]([OH:21])=[O:20])[CH2:10][O:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH3:18])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 1

HCID 131724098HCID 131724098, compound5×

Product 1

HCID 87222126HCID 87222126, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Nα-tert-butyloxycarbonyl-L-serine (4.59 g, 22.3 mmol) was dissolved in N,N-dimethylformamide (100 mL), the solution was then cooled to 0° C. and treated with sodium hydride (1.97 g, 49.2 mmol). 1-Bromo-2-(2-methoxyethoxy)ethane (10.0 g, 49.2 mmol) was added to the solution and the reaction mixture was stirred at ambient temperature for 3 h. The solvent was then removed under a reduced pressure at 40° C. bath temperature. The residue was dissolved in water (75 mL) and washed twice with diethyl ether (30 mL each time). The aqueous layer was then acidified to pH 3 with 1M HCl and then extracted with ethyl acetate. The organic layer was dried over anhydrous MgSO4 and the solvent was removed in vacuo to yield the compound as a yellow oil (4.1 g, 63%). The compound has the following characteristics: FTIR (CHCl3): 1735 (vCO, s), 1712 (vCO, s). 1H NMR (CDCl3): δ5.63 (d, (CH3)3COC(O)NHCH(CH2OCH2CH2OCH2CH2OCH3)C(O)OH, 1H), 4.38 (s, (CH3)3COC(O)NHCH(CH2OCH2CH2O—CH2CH2OCH3)C(O)OH, 1H), 4.14-3.53 (m, (CH3)3COC(O)NHCH(CH2OCH2CH2O—CH2CH2OCH3)C(O)OH, 10 H), 3.47 (s, (CH3)3COC(O)NHCH(CH2OCH2CH2OCH2—CH2OCH3)C(O)OH, 3H), 1.52 (s, (CH3)3COC(O)NHCH(CH2O—CH2CH2OCH2CH2—OCH3)C(O)OH, 9H). MALDITOF-MS: MH+: 307.34 calcd, 309.19 found.

Sources & evidence

ORD record
ord-2256cc306da444929d1c128745ca94a0
Source dataset
uspto-grants-2004_02
Patent number
US06686446B2

Reaction notes

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