1-Naphthalenemethanamine, alpha-methyl-, (alphaS)- → (S)-N-isoleucyl-4-allyloxybenzamide isopropyl ester

HRID 1165390Notes

Reaction equation

HRID 1165390 reaction equation
[CH2:1]([O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=O)=[CH:7][CH:6]=1)[CH:2]=[CH2:3].[NH2:14][C@H:15]([C:20]([O:22]C(C)C)=O)[C@H:16]([CH2:18][CH3:19])[CH3:17].[C:26]1([C@@H:36]([NH2:38])[CH3:37])C2C(=CC=CC=2)C=CC=1>>[CH:36]([N:38]([C:20](=[O:22])[C@H:15]([C@H:16]([CH2:18][CH3:19])[CH3:17])[NH2:14])[C:9](=[O:11])[C:8]1[CH:7]=[CH:6][C:5]([O:4][CH2:1][CH:2]=[CH2:3])=[CH:13][CH:12]=1)([CH3:37])[CH3:26]

Participants

4

Reactant 3

HCID 663251-Naphthalenemethanamine, alpha-methyl-, (alphaS)-HCID 4606904-(Prop-2-en-1-yloxy)benzoic acid2×HCID 22824829111278-90-1

Product 1

HCID 18638024(S)-N-isoleucyl-4-allyloxybenzamide isopropyl esterYield 54.1%

Procedure

(S)-N-Isoleucyl-4-allyloxybenzamide isopropyl ester was prepared as in Example 1 except 2.6 g (0.015 mole) of 4-allyloxybenzoic acid and 2.5 g (0.014 mole) of (S)-isopropyl isoleucinate were used in Example 2 rather than the 2.0 g of 4-allyloxybenzoic acid and 2 g (S)-1-(1-naphthyl)ethylamine in Example 1. The product was recrystallized twice from petroleum ether (30°-60°) to give 2.1 g (37%) of (S)-N-isoleucyl-4-allyloxybenzamide isopropyl ester as a white crystalline solid; mp 48°-48.5° C.; [α]D25 +48.93° (c=0.329, CHCl3); IR (KBr): 3300, 1725 and 1625 cm-1 ; NMR (δ): 0.96-1.12 (6H, m), 1.36 (6H, d, J=7.2 Hz), 1.40-1.76 (2H, m), (1H, broad, signal disappeared in D2O), 1.96-2.16 (1H, m,), 4.46 (2H, d, J=6.3 Hz), 4.74-5.20 (2H, m) 5.24-5.56 (2H, m) 5.88-6.28 (1H, m) 6.96 (2H, d, J=8.5 Hz), 7.80 (2H, d, J=8.5 Hz). Anal. for C19H27NO4 : Calcd: C, 68.47; H, 8.11; N, 4.20. Found: C, 68.50: H, 8.00; N, 4.30.

Workup

  1. customThe product was recrystallized twice from petroleum ether (30°-60°)

Sources & evidence

ORD record
ord-27fb18cf19894cc59d7fc4bbd3db33c8
Source dataset
uspto-grants-1990_03
Patent number
US04909935

Reaction notes

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