(2E)-5-(tert-Butyloxycarbonylamino)-5-methylhex-2-enoic acid → HCID 9829495, compound

HRID 380659Notes

Reaction equation

HRID 380659 reaction equation
[CH3:1][NH:2][C:3]([C:5]1([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:10][CH2:9][N:8]([C:11](=[O:26])[C@H:12]([NH:24][CH3:25])[CH2:13][C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=2)[CH2:7][CH2:6]1)=[O:4].C(OC([NH:41][C:42]([CH3:50])([CH3:49])[CH2:43]/[CH:44]=[CH:45]/[C:46](O)=[O:47])=O)(C)(C)C>>[CH3:1][NH:2][C:3]([C:5]1([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:10][CH2:9][N:8]([C:11](=[O:26])[C@H:12]([N:24]([C:46](=[O:47])/[CH:45]=[CH:44]/[CH2:43][C:42]([NH2:41])([CH3:50])[CH3:49])[CH3:25])[CH2:13][C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=2)[CH2:7][CH2:6]1)=[O:4]

Participants

3

Reactant 2

HCID 10847814(2E)-5-(tert-Butyloxycarbonylamino)-5-methylhex-2-enoic acidHCID 12151023HCID 12151023, compound

Product 1

HCID 9829495HCID 9829495, compound

Procedure

4-Benzyl-1-((2R)-2-methylamino-3-(2-naphthyl)propionyl)piperidine-4-carboxylic acid methylamide (360 mg; 0.82 mmole) was coupled to (2E)-5-(tert-butyloxycarbonylamino)-5-methyl-2-hexenoic acid using the same coupling procedure as in step D. Removal of the N-terminal Boc group was performed as in step D but at −10° C. The crude product was purified on a RP-18-Seppak® (5 g; Waters) using a gradient from 0.1% TFA in water/acetonitrile 100/0 to 0.1% TFA in 60/40 water/acetonitrile to afford 306 mg of the title compound as a trifluoroacetate.

Workup

  1. customRemoval of the N-terminal Boc group
  2. customwas performed as in step D but at −10° C
  3. customThe crude product was purified on a RP-18-Seppak® (5 g; Waters)

Sources & evidence

ORD record
ord-d5041a37c9e848b997bc670469e7b594
Source dataset
uspto-grants-2001_10
Patent number
US06303620B1

Reaction notes

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