Tetrahydrofuran → BocDTrp-Leu-MetNH2

HRID 2418579Notes

Reaction equation

HRID 2418579 reaction equation
C(N(CC)CC)C.O[N:9]1[C:13]2C=C[CH:16]=[CH:17][C:12]=2[N:11]=N1.C1(N=C=NC2CCCCC2)CCCCC1.[NH:33]([C:56]([O:58][C:59]([CH3:62])([CH3:61])[CH3:60])=[O:57])[C@@H:34]([C:45]([NH:47][C@H:48]([C:53](O)=[O:54])[CH2:49][CH:50]([CH3:52])[CH3:51])=[O:46])[CH2:35][C:36]1[C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[NH:38][CH:37]=1.N[C@H](C(N)=O)CC[CH2:67][S:68]C.Cl.[O:74]1CCCC1>>[NH:33]([C:56]([O:58][C:59]([CH3:62])([CH3:61])[CH3:60])=[O:57])[C@@H:34]([C:45]([NH:47][C@H:48]([C:53]([NH:11][C@H:12]([C:13]([NH2:9])=[O:74])[CH2:17][CH2:16][S:68][CH3:67])=[O:54])[CH2:49][CH:50]([CH3:52])[CH3:51])=[O:46])[CH2:35][C:36]1[C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[NH:38][CH:37]=1

Participants

7

Reactant 6

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 131713760BocDTrp-LeuOHHCID 131713761HMetNH2 hydrochloride

Product 1

HCID 131713756BocDTrp-Leu-MetNH2Yield 80%

Conditions

Temperature
0 °C

Procedure

Triethylamine (120 mmole.), then 1-hydroxybenzotriazole (60.0 mmole.), then dicyclohexylcarbodiimide (60.0 mmole.) were added with stirring to a solution of BocDTrp-LeuOH (59.9 mmole.) and HMetNH2 hydrochloride salt (60.0 mmole.) in tetrahydrofuran (300 ml.) with cooling to 0° C. Stirring was continued at 0° C. for one hour, then overnight while the mixture was allowed to warm to room temperature. The mixture was filtered and the filtrate was stripped of volatiles. Crystallization of the residue from isopropyl acetate affording BocDTrp-Leu-MetNH2 in 80% yield (26.3 g., m.r. 190°-194° C.).

Workup

  1. customovernight
  2. temperatureto warm to room temperature
  3. filtrationThe mixture was filtered
  4. customCrystallization of the residue from isopropyl acetate

Sources & evidence

ORD record
ord-27ec8c0c57924b87a3085309d1ac7a53
Source dataset
uspto-grants-1984_09
Patent number
US04472305

Reaction notes

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