Isobutyl chloroformate → HCID 101153814, compound

HRID 595246Notes

Reaction equation

HRID 595246 reaction equation
C(N(CC)C(C)C)(C)C.C(Cl)(=O)OCC(C)C.[C:18]([O:22][C:23]([NH:25][C@H:26]([CH3:30])[C:27]([OH:29])=O)=[O:24])([CH3:21])([CH3:20])[CH3:19].[Si]([CH:35]=[N+:36]=[N-:37])(C)(C)C>O1CCCC1.C(#N)C>[N+:36](=[CH:35][C:27](=[O:29])[C@H:26]([NH:25][C:23](=[O:24])[O:22][C:18]([CH3:19])([CH3:20])[CH3:21])[CH3:30])=[N-:37]

Participants

7

Reactant 4

HCID 62365Isobutyl chloroformateHCID 81531DiisopropylethylamineHCID 167693TrimethylsilyldiazomethaneHCID 637606BOC-D-alanine

Product 1

HCID 101153814HCID 101153814, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

N,N-Diisopropylethylamine (4.7 mL, 27 mmol) and isobutyl carbonochloridate (3.11 ml, 23.78 mmol) were added to a solution of (R)-2-((tert-butoxycarbonyl)amino)propanoic acid (3.0 g, 15.9 mmol) in tetrahydrofuran (34.5 ml) at 0° C. and the mixture was stirred at 0° C. for four hours. The mixture was then diluted with acetonitrile (22 mL). TMS-diazomethane (2.0 M in diethyl ether, 15.9 ml, 31.7 mmol) was then added slowly to the mixture at 0° C. The mixture was allowed to stir at 0° C. for 3 hours and was then allowed to warm to room temperature for 14 hours. The mixture was concentrated under reduced pressure and then purified by column chromatography on silica to afford (R)-tert-butyl (4-diazo-3-oxobutan-2-yl)carbamate. 1H NMR (500 MHz, DMSO-d6) δ 7.27 (d, J=7.4 Hz, 1H), 6.01 (s, 1H), 3.97-3.87 (m, 1H), 1.37 (s, 9H), 1.13 (d, J=7.3 Hz, 3H).

Workup

  1. stirringto stir at 0° C. for 3 hours
  2. temperatureto warm to room temperature for 14 hours
  3. concentrationThe mixture was concentrated under reduced pressure
  4. custompurified by column chromatography on silica

Sources & evidence

ORD record
ord-08bfd7e5dcae483193c67c9b02035efe
Source dataset
uspto-grants-2016_01
Patent number
US09242984B2

Reaction notes

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