1,2-Dichloroethane → HCID 131721924, compound

HRID 2269603Notes

Reaction equation

[NH:1]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:2][C:3]([N:5]1[CH2:20][CH2:19][CH2:18][C@H:6]1[C:7]([NH:9][C@H:10]([C:15](O)=[O:16])[CH2:11][CH2:12][CH2:13][CH3:14])=[O:8])=[O:4].[NH4+].[Cl-].C1C=CC2N(O)N=[N:36]C=2C=1.C(Cl)CCl>CN(C=O)C>[NH:1]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:2][C:3]([N:5]1[CH2:20][CH2:19][CH2:18][C@H:6]1[C:7]([NH:9][C@H:10]([C:15]([NH2:36])=[O:16])[CH2:11][CH2:12][CH2:13][CH3:14])=[O:8])=[O:4]

Participants

Conditions

Temperature: 0 °C

Procedure

Boc-Gly-Pro-Nleu-OH (4.1 g, 0.0106 mol.), NH4Cl (1.7 g, 0.032 mol.) and HOBt (1.76 g, 0.013 mol.) were dissolved in 100 ml DMF and the solution was chilled to 0° C. TEA (4.5 ml) was added to the solution slowly while stirring the solution. After a while, EDC (2.6 g, 0.013 mol.) was added to the solution. The stirring was continued overnight. The DMF was removed under reduced pressure and the resulting mixture was poured into 350 ml chloroform. The chloroform solution was washed by H2O 2×20 ml, saturated NaHCO3 2×20 ml, brine 2×20 ml, saturated NaHSO4 2×20 ml and brine again until the pH of the brine layer was approximate 7. The organic layer was dried using Na2SO4 and the chloroform was distilled under reduced pressure to obtain the product (3.5 g, 84%). TLC Rf=0.36 (developing solvents: CMA, 85:15:3).

Workup

customThe DMF was removed under reduced pressure
additionthe resulting mixture was poured into 350 ml chloroform
washThe chloroform solution was washed by H2O 2×20 ml, saturated NaHCO3 2×20 ml, brine 2×20 ml, saturated NaHSO4 2×20 ml and brine again until the pH of the brine layer
customThe organic layer was dried
distillationthe chloroform was distilled under reduced pressure

Sources & evidence

ORD record: ord-65586d2082a64f72a1a6b14e84ad39f7
Source dataset: uspto-grants-2001_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06329506B1

Reaction notes

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