Dichloromethane → HCID 131711581, compound

HRID 971853Notes

Reaction equation

[NH2:1][C@H:2]([C:10]([NH:12][C@H:13]([C:17]([NH:19][C@H:20]([C:23]([O:25][CH3:26])=[O:24])[CH2:21][OH:22])=[O:18])[C@@H:14]([CH3:16])[OH:15])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.FC([C:31]([OH:33])=[O:32])(F)F.C(Cl)Cl>C(N(CC)CC)C>[NH:12]([C:31]([O:33][C:4]([CH3:9])([CH3:5])[CH3:3])=[O:32])[C@H:13]([C:17]([NH:1][C@H:2]([C:10]([NH:12][C@H:13]([C:17]([NH:19][C@H:20]([C:23]([O:25][CH3:26])=[O:24])[CH2:21][OH:22])=[O:18])[C@@H:14]([CH3:16])[OH:15])=[O:11])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)=[O:18])[C@@H:14]([CH3:16])[OH:15]

Participants

Conditions

Temperature: 25 °C

Procedure

Phe-Thr-Ser-OMe.TFA, 6.4 g., and BOC-Thr-HSE, 4.6 g., is suspended in 100 ml. of methylene chloride. The reaction mixture is adjusted to a pH of 7 by the addition of triethylamine. After stirring the reaction mixture for 11/2 hours at 25° C., the crude product is isolated by filtration. The crude product is partially dissolved in 50 ml. methanol and precipitated by the addition of 450 ml. of ether. The partially purified product is isolated by filtration and this precipation process is repeated four times to give substantially pure BOC-Thr-Phe-Thr-Ser-OMe, 6.04 g.

Workup

customthe crude product is isolated by filtration
custommethanol and precipitated by the addition of 450 ml
customThe partially purified product is isolated by filtration

Sources & evidence

ORD record: ord-646bebd08d524749b51c9f6ba5f0297b
Source dataset: uspto-grants-1979_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04161521

Reaction notes

Loading…