Diisopropylethylamine → H-Gln(Trt)-Thr-Leu

HRID 1914978Notes

Reaction equation

HRID 1914978 reaction equation
[NH:1](C(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O)[C@H:2]([C:27](O)=[O:28])[CH2:3][CH2:4][C:5](=[O:26])[NH:6][C:7]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C.[NH2:83][C@H:84]([C:88]([NH:90][C@H:91]([C:96]([OH:98])=[O:97])[CH2:92][CH:93]([CH3:95])[CH3:94])=[O:89])[C@@H:85]([CH3:87])[OH:86]>CN(C=O)C>[NH2:1][C@H:2]([C:27]([NH:83][C@H:84]([C:88]([NH:90][C@H:91]([C:96]([OH:98])=[O:97])[CH2:92][CH:93]([CH3:94])[CH3:95])=[O:89])[C@@H:85]([CH3:87])[OH:86])=[O:28])[CH2:3][CH2:4][C:5](=[O:26])[NH:6][C:7]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 7021828Thr-LeuHCID 10919157(2S)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-4-[(triphenylmethyl)carbamoyl]butanoic acid

Product 1

HCID 131731099H-Gln(Trt)-Thr-Leu

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In an RBF were mixed Fmoc-Gln(Trt)-OH (44.7 g, 73.2 mmol), BOP (40.4 g, 91.5 mmol) and 250 ml of DMF. The mixture was stirred for 2 min and then DIPEA (18.9 g, 146.4 mmol) was added. The resulting mixture was added in one portion to the pre-swollen H-Thr-Leu-Resin and the reaction mixture was stirred for 2.5 h, the Kaiser test was negative, then the reaction was considered to be complete and the reaction medium was removed via filtration.

Workup

  1. stirringthe reaction mixture was stirred for 2.5 h
  2. customthe reaction medium was removed via filtration

Sources & evidence

ORD record
ord-8668ecaaf88c4afb830e81a1beb500e1
Source dataset
uspto-grants-2013_12
Patent number
US08614289B2

Reaction notes

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