Ethanolamine → N-((1S)-1-(4-hydroxyphenylmethyl)-2-chloroethyl)-N-isobutylammonium chloride

HRID 276497

Reaction equation

HRID 276497 reaction equation
OC1C=CC(C[C@H](N)CO)=CC=1.COC(=O)[C@H](CC1C=CC(O)=CC=1)N.OCCN.[CH:31]([CH:34]1[NH:38][C@@H:37]([CH2:39][C:40]2[CH:45]=[CH:44][C:43]([OH:46])=[CH:42][CH:41]=2)[CH2:36]O1)([CH3:33])[CH3:32].O1CCNC1.OC1C=CC(C[C@H](NCC(C)C)CO)=CC=1.O=S(Cl)[Cl:70]>>[Cl-:70].[OH:46][C:43]1[CH:44]=[CH:45][C:40]([CH2:39][C@H:37]([NH2+:38][CH2:34][CH:31]([CH3:33])[CH3:32])[CH2:36][Cl:70])=[CH:41][CH:42]=1

Participants

8

Reactant 7

HCID 700Ethanolamine2×HCID 24386Thionyl ChlorideHCID 70652Tyrosine Methyl EsterHCID 151247TyrosinolHCID 5366831,3-OxazolidineHCID 54421810N-((1S)-1-(4-hydroxyphenylmethyl)-2-hydroxyethyl)-N-isobutylamineHCID 57008578(4S)-2-isopropyl-4-(4-hydroxyphenylmethyl)-1,3-oxazolidine

Product 1

HCID 69992632N-((1S)-1-(4-hydroxyphenylmethyl)-2-chloroethyl)-N-isobutylammonium chloride

Procedure

(1S)-1-(4-Hydroxyphenylmethyl)-2-hydroxyethylamine was made from (L)-tyrosine methyl ester as described in Method B1b. The 2-hydroxyethylamine was converted to (4S)-2-isopropyl-4-(4-hydroxyphenylmethyl)-1,3-oxazolidine according to Method B4c, Step 1. The oxazolidine was reduced to N-((1S)-1-(4-hydroxyphenylmethyl)-2-hydroxyethyl)-N-isobutylamine according to Method B4c, Step 2. The resulting 2-hydroxyethylamine was treated with SOCl2 according to Method B7c to give N-((1S)-1-(4-hydroxyphenylmethyl)-2-chloroethyl)-N-isobutylammonium chloride. 2-Ethyl-4-cyanophenyl isothiocyanate was reacted with N-((1S)-1-(4-hydroxyphenylmethyl)-2-chloroethyl)-N-isobutylammonium chloride according to Method C1b to give (4S)-2-(2-ethyl-4-cyanophenylimino)-4-(4-hydroxyphenylmethyl)-3-isobutyl-1,3-thiazolidine HCl salt.

Sources & evidence

ORD record
ord-9910a369e89f4a6a8a28be5f89ac1ca4
Source dataset
uspto-grants-2002_03
Patent number
US06353006B1

Linked notes

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