Triethylamine → Z-Thr(tBu)-Phe-Pro-Gln-Thr(tBu)-Ala-Ile-Gly-OH

HRID 971553Notes

Reaction equation

HRID 971553 reaction equation
[NH:1]([C:31]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:32])[C@H:2]([C:10]([NH:12][C@H:13]([C:21]([N:23]1[CH2:30][CH2:29][CH2:28][C@H:24]1[C:25](O)=[O:26])=[O:22])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:11])[C@@H:3]([CH3:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6].C(N(CC)CC)C.C(Cl)(=O)OCC(C)C.[NH2:56][C@H:57]([C:63]([NH:65][C@H:66]([C:74]([NH:76][C@H:77]([C:79]([NH:81][C@H:82]([C:87]([NH:89][CH2:90][C:91]([OH:93])=[O:92])=[O:88])[C@H:83]([CH2:85][CH3:86])[CH3:84])=[O:80])[CH3:78])=[O:75])[C@@H:67]([CH3:73])[O:68][C:69]([CH3:72])([CH3:71])[CH3:70])=[O:64])[CH2:58][CH2:59][C:60](=[O:62])[NH2:61].Cl>O1CCCC1.CN(C)C=O.O>[NH:1]([C:31]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:32])[C@H:2]([C:10]([NH:12][C@H:13]([C:21]([N:23]1[CH2:30][CH2:29][CH2:28][C@H:24]1[C:25]([NH:56][C@H:57]([C:63]([NH:65][C@H:66]([C:74]([NH:76][C@H:77]([C:79]([NH:81][C@H:82]([C:87]([NH:89][CH2:90][C:91]([OH:93])=[O:92])=[O:88])[C@H:83]([CH2:85][CH3:86])[CH3:84])=[O:80])[CH3:78])=[O:75])[C@@H:67]([CH3:73])[O:68][C:69]([CH3:70])([CH3:71])[CH3:72])=[O:64])[CH2:58][CH2:59][C:60](=[O:62])[NH2:61])=[O:26])=[O:22])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:11])[C@@H:3]([CH3:9])[O:4][C:5]([CH3:7])([CH3:8])[CH3:6]

Participants

7

Reactant 4

HCID 8471Triethylamine2×HCID 62365Isobutyl chloroformateHCID 131709981Z-Thr(tBu)-Phe-Pro-OHHCID 131709982H-Gln-Thr(tBu)-Ala-Ile-Gly-OH.HCl

Product 1

HCID 131709980Z-Thr(tBu)-Phe-Pro-Gln-Thr(tBu)-Ala-Ile-Gly-OH

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21962138N,N-Dimethylformamide--water (1/1)Solvent

Conditions

Temperature
-10 °C

Procedure

2.8 g of Z-Thr(tBu)-Phe-Pro-OH and 0.77 ml of absolute triethylamine are dissolved in 30 ml of dry tetrahydrofurane and the solution, cooled to -10° C., is added dropwise to 700 mg of isobutyl chlorocarbonate, care being taken for the temperature not to exceed -5° C. The mixture is then left for 10 minutes at -10° C. and is thereafter added to a solution, precooled to -20° C., of 2.5 g of H-Gln-Thr(tBu)-Ala-Ile-Gly-OH.HCl in 65 ml of dimethylformamide-water (9:1). 1.2 ml of triethylamine are then added dropwise and the mixture is left for 1 hour at -10° C. and for 18 hours at 0° C. It is thereafter concentrated, in vacuo and then in a high vacuum at 40° C. bath temperature, to a volume of about 15 ml and then precipitated by adding 100 ml of ice-cold 2% strength acetic acid. The product is filtered off, washed with ice water, dried and twice reprecipitated from methanol-water to purify it; yield 3.9 g of octapeptide derivative.

Workup

  1. customto exceed -5° C
  2. additionis thereafter added to a solution
  3. waitthe mixture is left for 1 hour at -10° C. and for 18 hours at 0° C
  4. concentrationIt is thereafter concentrated, in vacuo
  5. customin a high vacuum at 40° C. bath temperature, to a volume of about 15 ml and then precipitated
  6. additionby adding 100 ml of ice-cold 2% strength acetic acid
  7. filtrationThe product is filtered off
  8. washwashed with ice water
  9. customdried
  10. customtwice reprecipitated from methanol-water
  11. customto purify it

Sources & evidence

ORD record
ord-3d44f548d0864ae6932fbb0a6f72adef
Source dataset
uspto-grants-1979_07
Patent number
US04159981

Reaction notes

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