1-Hydroxybenzotriazole → HCID 57936733, compound

HRID 1435095Notes

Reaction equation

HRID 1435095 reaction equation
[NH2:1][C@@H:2]([C:13]([NH:15][C@H:16]([C:29]([O:31][CH3:32])=[O:30])[CH2:17][CH2:18][CH2:19][CH2:20][NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[NH:33]([C:44]([O:46][CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)=[O:45])[C@H:34]([C:41](O)=[O:42])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.C1C=CC2N(O)N=NC=2C=1>C1COCC1>[NH:33]([C:44]([O:46][CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)=[O:45])[C@H:34]([C:41]([NH:1][C@@H:2]([C:13]([NH:15][C@H:16]([C:29]([O:31][CH3:32])=[O:30])[CH2:17][CH2:18][CH2:19][CH2:20][NH:21][C:22]([O:24][C:25]([CH3:26])([CH3:27])[CH3:28])=[O:23])=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1)=[O:42])[C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Participants

5

Reactant 3

HCID 757711-HydroxybenzotriazoleHCID 819214Z-Phg-OHHCID 15480274HCID 15480274, compound

Product 1

HCID 57936733HCID 57936733, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

17.0 g H-D-Trp-Lys(BOC)-OMe are mixed with 80 ml THF. 9.2 g Z-Phg-OH are added to the grey suspension at RT. Addition of 4.4 g HOBt, rinsing with 20 ml THF. The turbid yellow solution is cooled down to 0° and a solution of 5.3 ml DICI in 15 ml THF added within 10 minutes. Stirring 2 hours at 0°, then 2 hours at RT. Then addition of a solution of 3.6 sulfuric acid in 57 ml water, extraction with 70 ml ethyl acetate, washing with water, saturated brine, 5% sodium hydrogencarbonate, 25% brine, drying over MgSO4 and evaporation. The white residue is stirred in 125 ml isopropyl acetate 2 hours at 40° and the suspension filtered. Drying of the residue at 40°: slightly yellow substance. HPLC: 96.3% b.a. (25.3 min).

Workup

  1. washrinsing with 20 ml THF
  2. temperatureThe turbid yellow solution is cooled down to 0°
  3. additiona solution of 5.3 ml DICI in 15 ml THF added within 10 minutes
  4. custom2 hours
  5. customat RT
  6. additionThen addition of a solution of 3.6 sulfuric acid in 57 ml water, extraction with 70 ml ethyl acetate
  7. washwashing with water, saturated brine, 5% sodium hydrogencarbonate, 25% brine
  8. dry with materialdrying over MgSO4 and evaporation
  9. stirringThe white residue is stirred in 125 ml isopropyl acetate 2 hours at 40°
  10. filtrationthe suspension filtered
  11. customDrying of the residue at 40°
  12. custom(25.3 min)

Sources & evidence

ORD record
ord-054b89d37f264f08a28fb33568be2f30
Source dataset
uspto-grants-2009_11
Patent number
US07615609B2

Reaction notes

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