Triethylamine → Z-Thr(tBu)-Gln-Asn-Phe-OCH3

HRID 1580891Notes

Reaction equation

HRID 1580891 reaction equation
[NH2:1][C@H:2]([C:8]([NH:10][C@H:11]([C:16]([NH:18][C@H:19]([C:27]([O:29][CH3:30])=[O:28])[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:17])[CH2:12][C:13](=[O:15])[NH2:14])=[O:9])[CH2:3][CH2:4][C:5](=[O:7])[NH2:6].Cl.[CH3:32][C@@H:33]([O:56][C:57]([CH3:60])([CH3:59])[CH3:58])[C@H:34]([NH:45][C:46]([O:48][CH2:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)=[O:47])[C:35](ON1C(=O)CCC1=O)=[O:36].C(N(CC)CC)C>CN(C)C=O>[NH:45]([C:46]([O:48][CH2:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)=[O:47])[C@H:34]([C:35]([NH:1][C@H:2]([C:8]([NH:10][C@H:11]([C:16]([NH:18][C@H:19]([C:27]([O:29][CH3:30])=[O:28])[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:17])[CH2:12][C:13](=[O:15])[NH2:14])=[O:9])[CH2:3][CH2:4][C:5](=[O:7])[NH2:6])=[O:36])[C@@H:33]([CH3:32])[O:56][C:57]([CH3:59])([CH3:60])[CH3:58]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13503275Z-Thr(tBu)-OSUHCID 131709989H-Gln-Asn-Phe-OCH3 hydrochloride

Product 1

HCID 131709991Z-Thr(tBu)-Gln-Asn-Phe-OCH3

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

9.3 g of H-Gln-Asn-Phe-OCH3 hydrochloride and 11.9 g of Z-Thr(tBu)-OSU are dissolved in 150 ml of dimethylformamide to form a clear solution. 2.85 ml of triethylamine in 10 ml of dimethylformamide are added and the batch is stirred for 21 hours at room temperature. The batch is then concentrated under reduced pressure and taken up in much ethylacetate+chloroform (9:1), and extracted with 2 × 200 ml of 5% citric acid and 1 × 100 ml of water. The insoluble precipitate is then filtered off, the filtrate extracted with 2 × 200 ml of 2N-sodium carbonate solution and 3 × 100 ml of water, dried over sodium sulfate, and evaporated. The residue is recrystallized, together with the filter residue mentioned above, from dimethylformamide+ether (1:1). Melting point, 237°- 241°C (decomp.); [α]20D = + 8° (c = 1% in dimethylformamide).

Workup

  1. customto form a clear solution
  2. concentrationThe batch is then concentrated under reduced pressure
  3. extractionextracted with 2 × 200 ml of 5% citric acid and 1 × 100 ml of water
  4. filtrationThe insoluble precipitate is then filtered off
  5. extractionthe filtrate extracted with 2 × 200 ml of 2N-sodium carbonate solution and 3 × 100 ml of water
  6. dry with materialdried over sodium sulfate
  7. customevaporated
  8. customThe residue is recrystallized, together with the filter residue
  9. custom[α]20D = + 8° (c = 1% in dimethylformamide)

Sources & evidence

ORD record
ord-d295d202e6a5452992d950e0730dbfc9
Source dataset
uspto-grants-1976_01
Patent number
US03934008

Reaction notes

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