Tetrahydrofuran → HCID 15283082, compound

HRID 435397Notes

Reaction equation

C1COCC1.[NH:6]1[CH2:20][CH2:19][CH2:18][C@H:7]1[C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9].Cl.C1C=CC2N(O)N=NC=2C=1.[NH:32]([C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])[C@H:33]([C:43](O)=[O:44])[CH2:34][O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>CN(C=O)C>[NH:32]([C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])[C@H:33]([C:43]([N:6]1[CH2:20][CH2:19][CH2:18][C@H:7]1[C:8]([O:10][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)=[O:9])=[O:44])[CH2:34][O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

Conditions

Temperature: 0 °C

Procedure

THF (100 ml, H-Pro-OBzl.HCl (31.5 g, 0.13 M) and HOBT (17.5 g, 0.13 M) were added to BOC-Ser(Bzl)-OH (35.4 g, 0.12 M), and then DMF (50 ml) was added thereto to prepare a solution. WSCI (24.8 ml) was added dropwise and stirred at 0° C. for one hour and then at room temperature overnight. The solvent was distilled off in vacuo and benzene was added to the residue, which was then washed three times with 5% sodium bicarbonate solution, three times with 1 N HCl and three times with water, in that order. After drying with anhydrous sodium sulfate, the solution was dried in vacuo to obtain the substance [17] as an oil material (58 g, yield: 100%).

Workup

customto prepare a solution
additionWSCI (24.8 ml) was added dropwise
customat room temperature
customovernight
distillationThe solvent was distilled off in vacuo and benzene
additionwas added to the residue, which
washwas then washed three times with 5% sodium bicarbonate solution, three times with 1 N HCl and three times with water
dry with materialAfter drying with anhydrous sodium sulfate
customthe solution was dried in vacuo

Sources & evidence

ORD record: ord-b36f66daeb12411c8a55f30d0270fd04
Source dataset: uspto-grants-1983_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04400316

Reaction notes

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