Triethylamine → HCID 59597144, compound

HRID 2264888Notes

Reaction equation

HRID 2264888 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[CH:9]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([OH:21])[CH:16]=3)[NH:8][CH2:7][CH2:6][C:5]2=1.CCN(CC)CC.[NH:29]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH2:30][C:31](ON1C(=O)CCC1=O)=[O:32]>C1COCC1>[C:44]([O:43][C:41]([NH:29][CH2:30][C:31]([N:8]1[CH2:7][CH2:6][C:5]2[C:4]3[C:12](=[CH:13][CH:14]=[C:2]([CH3:1])[CH:3]=3)[NH:11][C:10]=2[CH:9]1[C:15]1[CH:16]=[C:17]([OH:21])[CH:18]=[CH:19][CH:20]=1)=[O:32])=[O:42])([CH3:47])([CH3:46])[CH3:45]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 76926N-(tert-Butyloxycarbonyl)glycine N-hydroxysuccinimide esterHCID 59597173HCID 59597173, compound

Product 1

HCID 59597144HCID 59597144, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-methyl-1-(3-hydroxyphenyl)-1,2,3,4-tetrahydro-beta-carboline (1 equiv) in THF was added Et3N (2.2 equiv) and Boc-Gly-OSu (1.2 equiv). After 2 h, the solvent was removed to give a residue, which was purified via prep-HPLC to give 3-{2-[N-(tert-butoxycarbonyl)-glycyl]-6-methyl-2,3,4,9-tetrahydro-1H-beta-carbolin-1-yl)}phenol 11.

Workup

  1. customthe solvent was removed
  2. customto give a residue, which
  3. customwas purified via prep-HPLC

Sources & evidence

ORD record
ord-bad34123d4f940ac98d6b608fd76fa81
Source dataset
uspto-grants-2010_12
Patent number
US07855295B2

Reaction notes

Loading…