Tetrahydrofuran → HCID 13091049, compound

HRID 435403Notes

Reaction equation

HRID 435403 reaction equation
C1COCC1.[NH:6]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C@H:7]([C:17]([OH:19])=O)[CH2:8][O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C1C=CC2N(O)N=NC=2C=1.[CH3:37][O:38][C:39]([C@@H:41]([NH2:51])[CH2:42][O:43][CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)=[O:40].Cl>CN(C=O)C>[NH:6]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C@H:7]([C:17]([NH:51][C@H:41]([C:39]([O:38][CH3:37])=[O:40])[CH2:42][O:43][CH2:44][C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=1)=[O:19])[CH2:8][O:9][CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 757711-HydroxybenzotriazoleHCID 90234L-Serine, N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)-HCID 44630138O-BENZYL-L-SERINE METHYL ESTER HYDROCHLORIDE

Product 1

HCID 13091049HCID 13091049, compoundYield 875.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

THF (700 ml) and BOC-Ser(Bzl)-OH (23.6 g, 0.8 M) and HOBT (108 g, 0.8 M) were added to H-Ser(Bzl)-Ome.HCl (196.57 g, 0.8 M); and DMF (200 ml) was added to prepare a solution. WSCI (146 ml, 0.8 M) was added dropwise thereto at 0° C. and the mixture was stirred at 0° C. for one hour and at room temperature overnight. The reaction mixture was concentrated in vacuo, and ethyl acetate (1 l.) was added to the residue, which was then washed with 5% sodium bicarbonate solution, 1 N HCl and water, each three times, in that order. Hexane was added to the oily product, which was then crystallized by adding crystalline seed. The material was then recrystallized from ether-hexane to obtain the substance [28] (340.4 g, yield: 87.5%).

Workup

  1. customto prepare a solution
  2. additionWSCI (146 ml, 0.8 M) was added dropwise
  3. concentrationThe reaction mixture was concentrated in vacuo, and ethyl acetate (1 l.)
  4. additionwas added to the residue, which
  5. washwas then washed with 5% sodium bicarbonate solution, 1 N HCl and water
  6. additionHexane was added to the oily product, which
  7. customwas then crystallized
  8. additionby adding crystalline seed
  9. customThe material was then recrystallized from ether-hexane

Sources & evidence

ORD record
ord-3fca5602cd2b43a4b2574f7af368fe6d
Source dataset
uspto-grants-1983_08
Patent number
US04400316

Reaction notes

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