Water → Carbamic acid, (cyanomethyl)-, 9H-fluoren-9-ylmethyl ester

HRID 489305Notes

Reaction equation

HRID 489305 reaction equation
Cl.[NH2:2][CH2:3][C:4]#[N:5].CCN(C(C)C)C(C)C.C(OC([O-])=O)(ON1C(=O)CC([C:24]([O:26][CH2:27][CH:28]2[C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[C:34]3[C:29]2=[CH:30][CH:31]=[CH:32][CH:33]=3)=[O:25])C1=O)=O.O>CN(C=O)C>[C:24]([NH:5][CH2:4][C:3]#[N:2])([O:26][CH2:27][CH:28]1[C:29]2[C:34](=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:35]2[C:40]1=[CH:39][CH:38]=[CH:37][CH:36]=2)=[O:25]

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 11491918Aminoacetonitrile hydrochlorideHCID 131725241HCID 131725241, compound

Product 1

HCID 11708912Carbamic acid, (cyanomethyl)-, 9H-fluoren-9-ylmethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Aminoacetonitrile HCL salt (1 mmol (92.53 mg)) is dissolved in DMF 2 ml and DIEA 2 mmol 0.35 ml. Then Fmoc-Succinimidyl dicarbonate 1.1 mmol, (350 mg) is added and the reaction allowed to proceed overnight. Water and diluted HCL is added to bring the pH to 2. The product is extracted 3 times with ethylacetate and dried over Na2SO4 to yield Fmoc-NH—CH2—CN. 1 mmol of the Fmoc-NH—CH2—CN (278 mg) is dissolved in 2 ml of anhydrous methanol bubbled with HCl gas. The reaction is kept at 0° C. for 40 hrs (Voss and Gerlach Helv. Chim. Acta (1983) 66: 2294) to yield the desired Fmoc-glycine orthotrimethylester (Fmoc-NH—CH2—C(OCH3)3).

Workup

  1. additionis added
  2. extractionThe product is extracted 3 times with ethylacetate
  3. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-e6872cfae0a24ee8a5fe356199315ce6
Source dataset
uspto-grants-2005_12
Patent number
US06977292B2

Reaction notes

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