(R)-2-(3-Chlorophenyl)-2-hydroxyacetic acid → N-[(2S)-7-hydroxy-1,2,3,4-tetrahydronaphth-2-yl]-(S)-3-chloromandelamide

HRID 2248989Notes

Reaction equation

HRID 2248989 reaction equation
[Cl:1]C1C=C(C=CC=1)[C@H](O)C(O)=O.[Cl:13][C:14]1[CH:15]=[C:16]([CH:22]=[CH:23][CH:24]=1)[C@@H:17]([OH:21])[C:18]([OH:20])=O.Cl.[NH2:26][C@H:27]1[CH2:36][CH2:35][C:34]2[C:29](=[CH:30][C:31]([OH:37])=[CH:32][CH:33]=2)[CH2:28]1>>[ClH:1].[NH2:26][C@@H:27]1[CH2:36][CH2:35][C:34]2[C:29](=[CH:30][C:31]([OH:37])=[CH:32][CH:33]=2)[CH2:28]1.[OH:37][C:31]1[CH:30]=[C:29]2[C:34]([CH2:35][CH2:36][C@H:27]([NH:26][C:18](=[O:20])[C@H:17]([C:16]3[CH:22]=[CH:23][CH:24]=[C:14]([Cl:13])[CH:15]=3)[OH:21])[CH2:28]2)=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 2733127(R)-2-(3-Chlorophenyl)-2-hydroxyacetic acidHCID 5324675(S)-2-(3-Chlorophenyl)-2-hydroxyacetic acidHCID 67824357(S)-7-Amino-5,6,7,8-tetrahydro-naphthalen-2-OL hydrochloride

Product 2

HCID 9973978N-[(2S)-7-hydroxy-1,2,3,4-tetrahydronaphth-2-yl]-(S)-3-chloromandelamideHCID 67824356(R)-7-Amino-5,6,7,8-tetrahydro-naphthalen-2-ol hydrochloride

Procedure

By following the procedure described in PREPARATION IX and substituting the (S)-3-chloromandelic acid for the (R)-3-chloromandelic acid and the (S)-2-amino-7-hydroxytetralin hydrochloride, PREPARATION IV, for the (R)-2-amino-7-hydroxytetralin hydrochloride, the N-[(2S)-7-hydroxy-1,2,3,4-tetrahydronaphth-2-yl]-(S)-3-chloromandelamide, SR 58574, is obtained; m.p. 145°-146° C.; |alpha|=-34.2° (methanol, c =1%).

Sources & evidence

ORD record
ord-eb6cc6c09f024a678f8c3775225eab9b
Source dataset
uspto-grants-1991_08
Patent number
US05041606

Reaction notes

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