TFA DCM MeOH → tert-Butyl 3-((2S)-amino-2-methoxycarbonylethyl)-2,4-dioxo-1,3,8-triazaspiro[4.5]decane-carboxylate

HRID 324601Notes

Reaction equation

HRID 324601 reaction equation
[CH3:1][O:2][C:3]([C@@H:5]([NH:26]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:6][N:7]1[C:11](=[O:12])[C:10]2([CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][CH2:13]2)[NH:9][C:8]1=[O:25])=[O:4].ClCCl.CO.FC(F)(F)[C:53]([OH:55])=[O:54]>>[NH2:26][C@H:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:6][N:7]1[C:11](=[O:12])[C:10]2([CH2:13][CH2:14][NH:15][CH2:16][CH2:17]2)[N:9]([C:53]([O:55][C:10]([CH3:17])([CH3:13])[CH3:11])=[O:54])[C:8]1=[O:25]

Participants

3

Reactant 2

HCID 19108260TFA DCM MeOHHCID 59093854HCID 59093854, compound

Product 1

HCID 86756622tert-Butyl 3-((2S)-amino-2-methoxycarbonylethyl)-2,4-dioxo-1,3,8-triazaspiro[4.5]decane-carboxylateYield 87%

Procedure

A solution of 4.6 g (7.5 mmol) of (34.4) in 180 ml of dichloromethane/methanol/trifluoroacetic acid=95.5/3/1.5 is stirred at room temperature for 10 min. The reaction mixture is concentrated and the residue is chromatographed through silica gel. 3.14 g (87%) of (34.5) are obtained after concentrating the product fractions.

Workup

  1. concentrationThe reaction mixture is concentrated
  2. customthe residue is chromatographed through silica gel

Sources & evidence

ORD record
ord-2bb6bb92fbb941909390f83c1beffc0b
Source dataset
uspto-grants-2001_04
Patent number
US06218415B1

Reaction notes

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