Ethanolamine → HCID 178428320, compound

HRID 276457Notes

Reaction equation

OC[C@@H](N)CC(C)C.COC(=O)[C@H](CC(C)C)N.OCCN.[CH3:23][C:24]1[CH:25]=[C:26]([CH:28]=[C:29]([CH3:34])[C:30]=1[N+:31]([O-:33])=[O:32])[NH2:27].[CH3:35][C:36]1[CH:37]=[C:38]([N:46]=[C:47]=[S:48])[CH:39]=C(C)[C:41]=1[N+]([O-])=O>>[CH3:34][C:29]1[CH:28]=[C:26]([N:27]=[C:47]2[NH:46][C@@H:38]([CH2:37][CH:36]([CH3:41])[CH3:35])[CH2:39][S:48]2)[CH:25]=[C:24]([CH3:23])[C:30]=1[N+:31]([O-:33])=[O:32]

Participants

Reactant 5

HCID 700Ethanolamine

HCID 369113,5-Dimethyl-4-nitroaniline

HCID 65105(+)-L-Leucine methyl ester

HCID 111307L-Leucinol

HCID 18316356HCID 18316356, compound2×

Product 1

HCID 178428320HCID 178428320, compound

Procedure

(1S)-1-(Hydroxymethyl)-3-methylbutylamine was made from (L)-leucine methyl ester as described in Method B1b. The 2-hydroxyethylamine was converted to (1S)-1-(chloromethyl)-3-methylbutanammonium chloride as described in Method B7a. 3,5-Dimethyl-4-nitroaniline was converted to 3,5-Dimethyl-4-nitrophenyl isothiocyanate according to Method A2a, Step 3. 3,5-Dimethyl-4-nitrophenyl isothiocyanate was reacted with (1S)-1-(chloromethyl)-3-methylbutanammonium chloride according to Method C1a to give (4S)-2-(3,5-dimethyl-4-nitrophenylimino)-4-isobutyl-1,3-thiazolidine. The thiazolidine was reacted with isobutyl bromide according to Method D2a to give (4S)-2-(3,5-dimethyl-4-nitrophenylimino)-3,4-diisobutyl-1,3-thiazolidine.

Sources & evidence

ORD record: ord-7f67b727f4274ec595be810e15dfdd6b
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06353006B1

Reaction notes

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