1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → Boc-Gly-Gly-Val-Pro-OBzl

HRID 2231795Notes

Reaction equation

HRID 2231795 reaction equation
N(C(OC(C)(C)C)=O)CC(N[C@H](C(N[CH2:13][C:14]([NH:16][C@H:17]([C:22]([N:24]1[CH2:38][CH2:37][CH2:36][C@H:25]1[C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27])=[O:23])[C@H:18]([CH2:20]C)[CH3:19])=[O:15])=O)C(C)C)=O.Cl.O1CCOCC1.[NH:53]([C:62]([O:64][C:65]([CH3:68])([CH3:67])[CH3:66])=[O:63])[CH2:54][C:55]([NH:57]CC(O)=O)=[O:56].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[NH:53]([C:62]([O:64][C:65]([CH3:68])([CH3:67])[CH3:66])=[O:63])[CH2:54][C:55]([NH:57][CH2:13][C:14]([NH:16][C@H:17]([C:22]([N:24]1[CH2:38][CH2:37][CH2:36][C@H:25]1[C:26]([O:28][CH2:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)=[O:27])=[O:23])[CH:18]([CH3:19])[CH3:20])=[O:15])=[O:56]

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 3334662-(2-{[(Tert-butoxy)carbonyl]amino}acetamido)acetic acidHCID 204431481,4-Dioxane hydrochlorideHCID 131715771Boc-Gly-Val-Gly-Ile-Pro-OBzl

Product 1

HCID 14306249Boc-Gly-Gly-Val-Pro-OBzl

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

III (6.0 g, 0.0148 mole) (39) was deblocked with HCl/Dioxane and solvent removed under reduced pressure. The residue was triturated with ether, filtered, washed with ether, then pet. ether and dried. A very hygroscopic material was obtained (4.2 g, 0.0123 mole) which was coupled in DMF with II (2.86 g, 0.0123 mole) in the presence of 10% excess of EDCI (2.60 g) and HOBt (2.07 g). The reaction was worked up as described for I to obtain IV as a white foam in a quantitative yield, no sharp m.p. 54°-62° C. Rf2, 0.42; Rf2, 0.74. Anal. Calcd. for C26H38N4O7 ; C, 60.21; H, 7.38; N, 10.80%. Found: C, 60.0; H, 7.46; N, 10.81%.

Workup

  1. customremoved under reduced pressure
  2. customThe residue was triturated with ether
  3. filtrationfiltered
  4. washwashed with ether
  5. dry with materialpet. ether and dried
  6. customA very hygroscopic material was obtained (4.2 g, 0.0123 mole) which

Sources & evidence

ORD record
ord-b384961f9cad4f0dab89ee1fa48e2fef
Source dataset
uspto-grants-1988_11
Patent number
US04783523

Reaction notes

Loading…