tert-Butyl (2S)-(adamant-1-ylmethoxycarbonylamino)-3-aminopropionate → 3(5-(((2s)-2-(1-Adamantylmethoxycarbonylamino)-2-tert-butoxycarbonyl-ethyl)carbamoyl)-2-thienyl)-acrylic acid methyl ester

HRID 431509Notes

Reaction equation

HRID 431509 reaction equation
[CH3:1][O:2][C:3]([CH:5]=[CH:6][C:7]1[S:11][C:10]([C:12]([OH:14])=O)=[CH:9][CH:8]=1)=[O:4].[C:15]([O:19][C:20](=[O:39])[C@@H:21]([NH:24][C:25]([O:27][CH2:28][C:29]12[CH2:38][CH:33]3[CH2:34][CH:35]([CH2:37][CH:31]([CH2:32]3)[CH2:30]1)[CH2:36]2)=[O:26])[CH2:22][NH2:23])([CH3:18])([CH3:17])[CH3:16]>C(OCC)(=O)C.CCCCCCC>[CH3:1][O:2][C:3](=[O:4])[CH:5]=[CH:6][C:7]1[S:11][C:10]([C:12](=[O:14])[NH:23][CH2:22][C@H:21]([NH:24][C:25]([O:27][CH2:28][C:29]23[CH2:36][CH:35]4[CH2:34][CH:33]([CH2:32][CH:31]([CH2:37]4)[CH2:30]2)[CH2:38]3)=[O:26])[C:20]([O:19][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:39])=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 53917304tert-Butyl (2S)-(adamant-1-ylmethoxycarbonylamino)-3-aminopropionateHCID 542089615-(2-Methoxycarbonyl-vinyl)-thiophene-2-carboxylic acid

Product 1

HCID 571433013(5-(((2s)-2-(1-Adamantylmethoxycarbonylamino)-2-tert-butoxycarbonyl-ethyl)carbamoyl)-2-thienyl)-acrylic acid methyl esterYield 32.4%

Reagents, catalysts & solvents 1

HCID 21899848Ethylacetate heptaneSolvent

Procedure

The title compound was synthesized analogously to example 3, step a) from 360 mg (1.84 mmol) of 5-(2-methoxycarbonyl-vinyl)-thiophene-2-carboxylic acid and 650 mg (1.84 mmol) of (2S)-2-(1-adamantylmethoxycarbonylamino)-3-amino-propionic acid tert-butyl ester. After chromatography (silica gel; ethyl acetate/n-heptane (1/1, v/v)) 326 mg of the title compound were obtained as colourless crystals.

Sources & evidence

ORD record
ord-29605b1cd5474ed1979905fa1cc2d23b
Source dataset
uspto-grants-2003_12
Patent number
US06660728B2

Reaction notes

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