Triethylamine → tert-butyl(S)-6-tert-butoxycarbonylamino-2-[3-((R)-1-carboxy-2-cyclohexyl-ethyl)-ureido]-hexanoate

HRID 1943298Notes

Reaction equation

HRID 1943298 reaction equation
Cl.[NH2:2][C@@H:3]([CH2:11][CH2:12][CH2:13][CH2:14][NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].CCN(CC)CC.[C:30](N1C=CN=C1)(N1C=CN=C1)=[O:31].FC(F)(F)C(O)=O.[NH2:49][C@H:50]([CH2:54][CH:55]1[CH2:60][CH2:59][CH2:58][CH2:57][CH2:56]1)[C:51]([OH:53])=[O:52].[N-]1C=CN=C1>CN(C=O)C>[C:19]([O:18][C:16]([NH:15][CH2:14][CH2:13][CH2:12][CH2:11][C@H:3]([NH:2][C:30]([NH:49][C@@H:50]([C:51]([OH:53])=[O:52])[CH2:54][CH:55]1[CH2:60][CH2:59][CH2:58][CH2:57][CH2:56]1)=[O:31])[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5])=[O:17])([CH3:22])([CH3:21])[CH3:20]

Participants

7

Reactant 5

HCID 8471Triethylamine2×HCID 682631,1'-CarbonyldiimidazoleHCID 3386966ImidazolateHCID 1381988513288-57-8HCID 68547671(R)-2-Amino-3-cyclohexylpropanoic acid trifluoroacetate

Product 1

HCID 68548206tert-butyl(S)-6-tert-butoxycarbonylamino-2-[3-((R)-1-carboxy-2-cyclohexyl-ethyl)-ureido]-hexanoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Commercial tert-butyl(S)-2-amino-6-tert-butoxycarbonylaminohexanoate hydrochloride (1.95 g, 5.75 mmol) was mixed in 30 ml of DMF with NEt3 (0.8 ml, 5.754 mmol) and 1,1′-carbonyldiimidazole (0.933 g, 5.754 mmol) and stirred at RT for 30 min. Then (R)-2-amino-3-cyclohexylpropanoic acid trifluoroacetate (1.64 g, 5.754 mmol) and NEt3 (1.6 ml, 11.5 mmol) were added, and the mixture was heated at 80° C. until the imidazolide formed as intermediate was completely converted. The product was purified by flash chromatography on silica gel (CH2Cl2/MeOH gradient). Yield: 2.1 g (73%) of tert-butyl(S)-6-tert-butoxycarbonylamino-2-[3-((R)-1-carboxy-2-cyclohexylethyl)-ureido]-hexanoate.

Workup

  1. customformed as intermediate
  2. customThe product was purified by flash chromatography on silica gel (CH2Cl2/MeOH gradient)

Sources & evidence

ORD record
ord-1d9c02088d4f41399aa678518c4e5865
Source dataset
uspto-grants-2013_03
Patent number
US08389764B2

Reaction notes

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