Diisopropylcarbodiimide → 5-{2-[(2-tert-Butoxycarbonyl-ethyl)-(17-tert-butoxycarbonyl-heptadecanoyl)-amino]-acetylamino}-isophthalic acid mono-tert-butyl ester

HRID 562536Notes

Reaction equation

HRID 562536 reaction equation
[C:1]([O:5][C:6](=[O:39])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23](=[O:38])[N:24]([CH2:29][CH2:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:25][C:26]([OH:28])=O)([CH3:4])([CH3:3])[CH3:2].C1C=NC2N(O)N=NC=2C=1.CC(C)N=C=NC(C)C.[C:59]([O:63][C:64](=[O:75])[C:65]1[CH:73]=[C:72]([NH2:74])[CH:71]=[C:67]([C:68]([OH:70])=[O:69])[CH:66]=1)([CH3:62])([CH3:61])[CH3:60].CCN(C(C)C)C(C)C>C(Cl)Cl>[C:59]([O:63][C:64](=[O:75])[C:65]1[CH:73]=[C:72]([NH:74][C:26](=[O:28])[CH2:25][N:24]([CH2:29][CH2:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[C:23](=[O:38])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:39])[CH:71]=[C:67]([C:68]([OH:70])=[O:69])[CH:66]=1)([CH3:62])([CH3:60])[CH3:61]

Participants

7

Reactant 5

HCID 12734DiisopropylcarbodiimideHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 866192463-Amino-5-(tert-butoxycarbonyl)benzoic acidHCID 8661924817-[(2-tert-Butoxycarbonyl-ethyl)-carboxymethyl-carbamoyl]-heptadecanoic acid tert-butyl ester

Product 1

HCID 667244995-{2-[(2-tert-Butoxycarbonyl-ethyl)-(17-tert-butoxycarbonyl-heptadecanoyl)-amino]-acetylamino}-isophthalic acid mono-tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

17-[(2-tert-Butoxycarbonyl-ethyl)-carboxymethyl-carbamoyl]-heptadecanoic acid tert-butyl ester (0.130 g) was dissolved in dry DCM (5 ml). HOAt (0.36 mg) and DIC (0.045 ml) was added the mixture was refluxed for 1 h under nitrogen. The reaction mixture was cooled to room temperature and 5-amino-isophthalic acid mono t-Butyl ester (60 mg) was added. After stirring for 1 h DIPEA (0.050 ml) was added, the orange reaction mixture turns yellow. After stirring for 2 days, the reaction mixture was concentrated. The residue was redissolved in EtOAc and extracted with 0.1 N HCl (2×) and brine (1×), dried (Na2SO4), and concentrated to give an sirup, which solidifies on standing. 5-{2-[(2-tert-Butoxycarbonyl-ethyl)-(17-tert-butoxycarbonyl-heptadecanoyl)-amino]-acetylamino}-isophthalic acid mono-tert-butyl ester was obtained in a quantitative yield (214 mg), contaminated with an impurity. HPLC/MS 775 (M), rt 7.64 min.

Workup

  1. temperaturewas refluxed for 1 h under nitrogen
  2. additionwas added
  3. concentrationthe reaction mixture was concentrated
  4. dissolutionThe residue was redissolved in EtOAc
  5. extractionextracted with 0.1 N HCl (2×) and brine (1×)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customto give an sirup, which

Sources & evidence

ORD record
ord-2770cfbe1f6f4d6785f145776425d731
Source dataset
uspto-grants-2011_11
Patent number
US08067362B2

Reaction notes

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