Methyl L-phenylalaninate hydrochloride → HCID 6999129, compound

HRID 1450727Notes

Reaction equation

HRID 1450727 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:14])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[NH2:6].[NH:15]([C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22])[C@H:16]([C:18](O)=[O:19])[CH3:17]>C1COCC1>[NH:15]([C:21]([O:23][CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)=[O:22])[C@H:16]([C:18]([NH:6][C@H:5]([C:4]([O:3][CH3:2])=[O:14])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:19])[CH3:17]

Participants

4

Reactant 2

HCID 75736Methyl L-phenylalaninate hydrochlorideHCID 736104N-carbobenzyloxyalanine

Product 1

HCID 6999129HCID 6999129, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Phenylalanine methyl ester hydrochloride (0.5 g, 2.3 mmol) was suspended in 10 mL of dry THF. Et3 n (0.35 mL, 2.5 mol) was added, after which both CBZ-Ala (10, 0.52 g, 100 mol %) and 1 (0.65 g, 104 mol %) were also added. The reaction mixture was stirred for 24 h at room temperature. Following the general procedure gave 21, 0.74 g, 84%, as a crystalline solid. An identical reaction using DMF as the solvent produced 21 in 93% yield: mp 97°-98° C.; [α]25D -8.3° (c 0.3, EtOH); 1H NMR δ 7.42-7.15 (m, 10H), 6.40 (d, 1H, J=4), 5.24-5.21 (m, 1H), 5.10 (s, 2H), 4.88-4.84 (m, 1H), 4.24-4.21 (m, 1H), 3.78 (s, 3H), 3.16-3.13 (m, 2H), 1.38 (d, 3H, J=7). Anal. Calcd for C21H24N3O5 : C, 65.5; H, 6.3,; N, 7.3. Found: C, 65.5; H, 6.3; N, 7.3. Compound 21 was also synthesized from the reaction of 11 and isourea 2 (R=M1) in DMF (82% yield) and was identical to material formed above.

Workup

  1. additionEt3 n (0.35 mL, 2.5 mol) was added

Sources & evidence

ORD record
ord-ac6a51c9445a4f80b5f9c3c017d85489
Source dataset
uspto-grants-1997_02
Patent number
US05602264

Reaction notes

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