1,2-Dichloroethane → Boc-Ala-Gly-Gly-OBzl

HRID 1379602Notes

Reaction equation

HRID 1379602 reaction equation
C(Cl)CCl.[NH:5]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C@H:6]([C:8]([NH:10][CH2:11][C:12]([OH:14])=O)=[O:9])[CH3:7].[NH2:22][CH2:23][C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25].C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1>C(Cl)Cl>[NH:5]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C@H:6]([C:8]([NH:10][CH2:11][C:12]([NH:22][CH2:23][C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25])=[O:14])=[O:9])[CH3:7]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 192414(S)-2-(2-((tert-Butoxycarbonyl)amino)propanamido)acetic acidHCID 409140Benzyl glycinate

Product 1

HCID 131720212Boc-Ala-Gly-Gly-OBzl

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

One equivalent of 0.39 g (2 mmol) EDC (Aldrich) is added into a stirred solution of 0.5 g (2 mmol) of Boc Ala-Gly-OH (12), 0.4 g of (2 mmol) of Gly-OBzl (Sigma), 0.27 g of HOBT (Aldrich), and 0.2 ml of NMM in 100 ml of DCM at ice bath temperature. The reaction mixture is stirred for 3 h at 0° C. and 22 h at ambient temperature. The reaction mixture is concentrated using a rotary evaporator, and the residue is dissolved in 100 ml of ethyl acetate. The ethyl acetate solution is extracted with 10% NaHCO3 and water. The organic layer is dried over anhydrous Na2SO4 and isolated by decantation. Then, the ethyl acetate is evaporated to furnish the Boc-Ala-Gly-Gly-OBzl (13) as a yellow oil which is confirmed by MS and NMR. 1H-NMR (CDCl3): 1.28 (3H, d, J=7.2 Hz), 1.31 (9H, s), 3.85-4.15 (5H, m), 5.06 (2H, s), 5.45 (1H, br), 7.25 (5H, br), 7.41 (1H, br). FABMS: 394 (M+1).

Workup

  1. concentrationThe reaction mixture is concentrated
  2. customa rotary evaporator
  3. dissolutionthe residue is dissolved in 100 ml of ethyl acetate
  4. extractionThe ethyl acetate solution is extracted with 10% NaHCO3 and water
  5. dry with materialThe organic layer is dried over anhydrous Na2SO4
  6. customisolated by decantation
  7. customThen, the ethyl acetate is evaporated

Sources & evidence

ORD record
ord-063f9131901b49019387d3c35b9c092e
Source dataset
uspto-grants-1997_09
Patent number
US05672584

Reaction notes

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