Triethylamine → BOC-D-Lys(Z)-GlyNH2

HRID 1982652Notes

Reaction equation

HRID 1982652 reaction equation
[NH2:1][CH2:2][C:3]([NH2:5])=[O:4].Cl.CCN(CC)CC.C1C=CC2N(O)N=NC=2C=1.[NH:24]([C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[C@@H:25]([C:41]([OH:43])=O)[CH2:26][CH2:27][CH2:28][CH2:29][NH:30][C:31]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:32].NCC(N)=O>CN(C=O)C>[NH:24]([C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[C@@H:25]([C:41]([NH:1][CH2:2][C:3]([NH2:5])=[O:4])=[O:43])[CH2:26][CH2:27][CH2:28][CH2:29][NH:30][C:31]([O:33][CH2:34][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)=[O:32]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 69020GlycinamideHCID 757711-HydroxybenzotriazoleHCID 2723639Glycinamide hydrochlorideHCID 7269335(2R)-6-{[(benzyloxy)carbonyl]amino}-2-{[(tert-butoxy)carbonyl]amino}hexanoic acid

Product 1

HCID 131714761BOC-D-Lys(Z)-GlyNH2Yield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

GlyNH2.HCl (2.65 g, 0.024 mol) is dispersed in DMF and to this is added Et3N (3.35 ml, 0.024 mol) and HOBT (3.7 g, 0.024 mol). 9.0 g (0.024 mol) of BOC-D-Lys(Z) in a large volume of DMF is added and the GlyNH2 goes into solution. The total volume of DMF is 400 ml. The reaction is stirred overnight and then filtered. The solvent is evaporated off and the residue dissolved in CH2Cl2. This is washed with citric acid solution, Na2CO3 solution and then NaCl solution, and dried with MgSO4. The mixture is filtered, the filtrate evaporated down and the residue is taken up in ethyl acetate and cooled. The solid is filtered and washed with pet ether. More solid is obtained from the filtrate. Both crops are combined and triturated with ether. 7.5 g of a tan, solid is obtained in a 71% yield:

Workup

  1. filtrationfiltered
  2. customThe solvent is evaporated off
  3. dissolutionthe residue dissolved in CH2Cl2
  4. washThis is washed with citric acid solution, Na2CO3 solution
  5. dry with materialNaCl solution, and dried with MgSO4
  6. filtrationThe mixture is filtered
  7. customthe filtrate evaporated down
  8. temperaturecooled
  9. filtrationThe solid is filtered
  10. washwashed with pet ether
  11. customMore solid is obtained from the filtrate
  12. customtriturated with ether
  13. custom7.5 g of a tan, solid is obtained in a 71% yield

Sources & evidence

ORD record
ord-d3e300d9ac6049fcada91323f385825e
Source dataset
uspto-grants-1986_06
Patent number
US04596819

Reaction notes

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