Isobutyl chloroformate → HCID 178512905, compound

HRID 1679645Notes

Reaction equation

HRID 1679645 reaction equation
[NH2:1][C@H:2]([C:10]([OH:12])=O)[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:9])[NH2:8].C(OC(N([N+]([O-])=O)[C@H](C(O)=O)CCCNC(=N)N)=O)(C)(C)C.C(Cl)(=O)OCC(C)C.[NH2:43][CH2:44][C:45]([NH2:47])=[O:46]>CN(C)C=O.O1CCCC1.C(N(CC)CC)C>[NH2:1][C@H:2]([C:10]([NH:43][CH2:44][C:45]([NH2:47])=[O:46])=[O:12])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:9])[NH2:8]

Participants

8

Reactant 4

HCID 62365Isobutyl chloroformateHCID 69020GlycinamideHCID 178418600HCID 178418600, compoundHCID 178454196HCID 178454196, compound

Product 1

HCID 178512905HCID 178512905, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolvent2×HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

Protected arginine, i.e., tert-butyloxycarbonylnitro-arginine is dissolved in a suitable solvent such as dimethylformamide and tetrahydrofuran. The dissolved protected amino acid is then cooled to a temperature slightly below the freezing point (0° C), whereupon isobutyl chlorocarbonate and triethylamine is added with stirring. After a short period, glycinamide dissolved in dimethylformamide is added. The mixture is then permitted to warm to room temperature and stirred for a period of several hours and then filtered. The filtrate is recovered and evaporated to dryness and then extracted with dimethylformamide. The dimethylformamide solution is precipitated with ethylacetate to yield the dipeptide, i.e., protected arginyl-glycinamide.

Workup

  1. additionis added
  2. waitAfter a short period
  3. additionis added
  4. stirringstirred for a period of several hours
  5. filtrationfiltered
  6. customThe filtrate is recovered
  7. customevaporated to dryness
  8. extractionextracted with dimethylformamide
  9. customThe dimethylformamide solution is precipitated with ethylacetate

Sources & evidence

ORD record
ord-55a5380ecac242509ecaf254a4a52585
Source dataset
uspto-grants-1978_03
Patent number
US04081533

Reaction notes

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