Tetrahydrofuran → Boc-prolylproline benzyl ester

HRID 435400Notes

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.[N:32]1([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:39][CH2:38][CH2:37][C@H:33]1[C:34](O)=[O:35]>CN(C=O)C>[N:32]1([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:39][CH2:38][CH2:37][C@H:33]1[C:34]([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:35]

Participants

Conditions

Temperature: 0 °C

Procedure

THF (180 ml), H-Pro-OBzl.HCl (43.5 g, 0.18 M) and HOBT (24.3 g, 0.18 M) were added to BOC-Pro-OH (36.6 g, 0.17 M); DMF (100 ml) was added, and WSCI (33.0 ml, 0.18 M) was added dropwise at 0° C. After stirring at 0° C. for one hour and at room temperature overnight, the solvent was distilled off in vacuo. Benzene (500 ml) was added to the residue, which was washed three times with 5% sodium bicarbonate, three times with 1 N HCl and three times with water, in that order. After drying with anhydrous sodium sulfate, the solution was concentrated in vacuo to obtain the oily material [23] (74 g, yield: 100%).

Workup

additionWSCI (33.0 ml, 0.18 M) was added dropwise at 0° C
distillationthe solvent was distilled off in vacuo
additionBenzene (500 ml) was added to the residue, which
washwas washed three times with 5% sodium bicarbonate, three times with 1 N HCl and three times with water
dry with materialAfter drying with anhydrous sodium sulfate
concentrationthe solution was concentrated in vacuo

Sources & evidence

ORD record: ord-3ef32cafce9148c6b68ee407fd4aaed0
Source dataset: uspto-grants-1983_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04400316

Reaction notes

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