(R)-2-Amino-3-chloropropanoic acid hydrochloride → 9-(2-Amino-2-carboxy-ethylthio)-3-(2-(3-furyl)ethyl)-spiro[5.5]undecane

HRID 1757223Notes

Reaction equation

HRID 1757223 reaction equation
[SH:1][CH:2]1[CH2:19][CH2:18][C:5]2([CH2:10][CH2:9][CH:8]([CH2:11][CH2:12][C:13]3[CH:17]=[CH:16][O:15][CH:14]=3)[CH2:7][CH2:6]2)[CH2:4][CH2:3]1.Cl.Cl[CH2:22][C@@H:23]([C:25]([OH:27])=[O:26])[NH2:24]>>[NH2:24][CH:23]([C:25]([OH:27])=[O:26])[CH2:22][S:1][CH:2]1[CH2:3][CH2:4][C:5]2([CH2:6][CH2:7][CH:8]([CH2:11][CH2:12][C:13]3[CH:17]=[CH:16][O:15][CH:14]=3)[CH2:9][CH2:10]2)[CH2:18][CH2:19]1

Participants

3

Reactant 2

HCID 11957493(R)-2-Amino-3-chloropropanoic acid hydrochlorideHCID 152348549-Mercapto-3-(2-(3-furyl)ethyl)-spiro[5.5]undecane

Product 1

HCID 152348369-(2-Amino-2-carboxy-ethylthio)-3-(2-(3-furyl)ethyl)-spiro[5.5]undecane

Procedure

Using the experimental conditions described in Ex. 24 and 9-mercapto-3-(2-(3-furyl)ethyl)-spiro[5.5]undecane and 3-chloroalanine hydrochloride as starting materials, the title compound (I-aa) was obtained as an amorphous solid. TLC: Rf=0.28 (SiO2 plates, n-butanol/acetic acid/water 40/10/50). 1H-NMR (300 MHz, CDCl3, ppm from TMS): 7.37 (1H, m), 7.24 (1H, m), 6.26 (1H, m), 4.4-4.2 (3H, m), 3.48 (1H, m), 2.70 (1H, m), 2.45 (2H, t), 2.42 (2H, t), 1.90-0.85 (19H, m).

Sources & evidence

ORD record
ord-67a9759f886143f7a8fce1f7985bad92
Source dataset
uspto-grants-1995_08
Patent number
US05444082

Reaction notes

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