17-{3-[(2-Benzyloxycarbonylethyl)tert-butoxycarbonylamino]propionylamino}heptadecanoic acid tert-butyl ester → 17-{3-[tert-Butoxycarbonyl (2-carboxyethyl)amino]propionylamino}heptadecanoic acid tert-butyl ester

HRID 2369796Notes

Reaction equation

HRID 2369796 reaction equation
[C:1]([O:5][C:6](=[O:48])[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][NH:23][C:24](=[O:47])[CH2:25][CH2:26][N:27]([CH2:35][CH2:36][C:37]([O:39]CC1C=CC=CC=1)=[O:38])[C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])([CH3:4])([CH3:3])[CH3:2]>C1COCC1>[C:1]([O:5][C:6](=[O:48])[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][NH:23][C:24](=[O:47])[CH2:25][CH2:26][N:27]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:35][CH2:36][C:37]([OH:39])=[O:38])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 1

HCID 6876904917-{3-[(2-Benzyloxycarbonylethyl)tert-butoxycarbonylamino]propionylamino}heptadecanoic acid tert-butyl ester

Product 1

HCID 8664713017-{3-[tert-Butoxycarbonyl (2-carboxyethyl)amino]propionylamino}heptadecanoic acid tert-butyl esterYield 102.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

17-{3-[(2-Benzyloxycarbonylethyl)tert-butoxycarbonylamino]propionylamino}heptadecanoic acid tert-butyl ester (0.135 g, 0.2 mmol) was dissolved in THF (10 mL) in a flask. The flask was filled with nitrogen and purged under vacuum several times. Pd/C, wet 10% (0.03 g) was added and the flask was equipped with a balloon filled with the mixture was stirred for 16 h. The mixture was filtered through a celite, eluting with THF. The filtrate was concentrated under vacuum. TLC indicated the reaction was not complete, so the process was repeated twice more. The filtrate was concentrated under vacuum to yield a yellow oil (0.12 g)

Workup

  1. additionThe flask was filled with nitrogen
  2. custompurged under vacuum several times
  3. additionPd/C, wet 10% (0.03 g) was added
  4. customthe flask was equipped with a balloon
  5. additionfilled with the mixture
  6. filtrationThe mixture was filtered through a celite
  7. washeluting with THF
  8. concentrationThe filtrate was concentrated under vacuum
  9. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-a56a7a4af1394f78af270315569bf34c
Source dataset
uspto-grants-2014_04
Patent number
US08710000B2

Reaction notes

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