Hydrochloric Acid → HCID 15567213, compound

HRID 986349Notes

Reaction equation

HRID 986349 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:17]([OH:19])=O)[CH2:13][C:14](=[O:16])[NH2:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N1CCCCC1)C.C(Cl)(=O)C(C)(C)C.[CH3:35][O:36][C:37](=[O:47])[C@H:38]([CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[NH2:39].Cl>ClCCl.N1C=CC=CC=1>[CH3:35][O:36][C:37](=[O:47])[C@H:38]([CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[NH:39][C:17](=[O:19])[C@H:12]([CH2:13][C:14](=[O:16])[NH2:15])[NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 13007N-Ethylpiperidine2×HCID 62493Pivaloyl chlorideHCID 75314Benzyloxycarbonyl-asparagineHCID 736234L-Phenylalanine, methyl ester

Product 1

HCID 15567213HCID 15567213, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of benzyloxycarbonylasparagine (13.3 g; 50 mmoles), N-ethylpiperidine (7.0 ml) and pyridine (5.0 ml) in dichloromethane (100 ml) cooled to -20° C. is treated under constant stirring with pivaloylchloride (6.3 ml); the mixture is then stirred and cooled (0° C.) for 8 minutes. After that, within 2 to 3 minutes, a solution of phenylalanine methyl ester, liberated from its hydrochloride (10.7 g; 50 mmoles) by the addition of N-ethylpiperidine (7.0 ml), in dichlormethane (100 ml) is added. The reaction mixture is stirred for an additional 2 hours at room temperature, the precipitated crystalline substance is collected on filter and triturated successively with 1 M hydrochloric acid, water, 5% aqueous sodium hydrogencarbonate solution and water. Crystallization from methanol yields 14.5 g (68%) of the title product, melting at 196° -197° C. An analytical sample is crystallized from dimethylformamide and 2-propanol, and the m.p. remains unchanged. Chromatography: Rf 0.71/S1, 0.75/S2. Optical rotation [α]D20 -2.0° (c 0.2; dimethylformamide). The elemental composition corresponds to the summary formula C22H25N3O6.

Workup

  1. additionis treated
  2. additionis added
  3. stirringThe reaction mixture is stirred for an additional 2 hours at room temperature
  4. customthe precipitated crystalline substance is collected
  5. filtrationon filter
  6. customtriturated successively with 1 M hydrochloric acid, water, 5% aqueous sodium hydrogencarbonate solution and water
  7. customCrystallization from methanol

Sources & evidence

ORD record
ord-3e2fcb5200624d39b58d4f19a70bc78a
Source dataset
uspto-grants-1987_12
Patent number
US04711952

Reaction notes

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