1-Hydroxybenzotriazole → t-Butyloxycarbonyl-L-alanyl-L-valyl-Nepsilon-benzyloxycarbonyl-L-lysine benzyl ester

HRID 1732522Notes

Reaction equation

HRID 1732522 reaction equation
[CH2:1]([O:8][C:9](=[O:41])[C@H:10]([CH2:26][CH2:27][CH2:28][CH2:29][NH:30][C:31]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:32])[NH:11][C:12](=[O:25])[C@H:13]([CH:22]([CH3:24])[CH3:23])NC(OC(C)(C)C)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC[N:44](C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.[NH:61]([C:76]([O:78][C:79]([CH3:82])([CH3:81])[CH3:80])=[O:77])[C@H:62]([C:64](OC1C=CC([N+]([O-])=O)=CC=1)=[O:65])[CH3:63]>CN(C=O)C>[CH2:1]([O:8][C:9](=[O:41])[C@H:10]([CH2:26][CH2:27][CH2:28][CH2:29][NH:30][C:31]([O:33][CH2:34][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)=[O:32])[NH:11][C:12](=[O:25])[C@H:13]([CH:22]([CH3:23])[CH3:24])[NH:44][C:64](=[O:65])[C@H:62]([CH3:63])[NH:61][C:76]([O:78][C:79]([CH3:82])([CH3:81])[CH3:80])=[O:77])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 7021877Boc-Ala-ONpHCID 131711965t-Butyloxycarbonyl-L-valyl-Nepsilon-benzyloxycarbonyl-L-lysine benzyl ester

Product 1

HCID 131711964t-Butyloxycarbonyl-L-alanyl-L-valyl-Nepsilon-benzyloxycarbonyl-L-lysine benzyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The Boc group was removed from a sample (3.8 g, 6.6 mmole) of compound XX as described above. The partially deprotected 2-peptide ester (trifluoroacetate salt) was dissolved in DMF (60 ml) and treated with DIEA (2.4 ml, 15 mmole), HOBt (1.18 g, 7.7 mmole) and Boc-L-Ala-ONp (2.38 g, 7.7 mmole, Bachem) at 0°. After overnight storage at room temperature a semisolid mass formed. Most of the solvent was removed in vacuo, the residue triturated with EtOAc and with ether and dried: 3.6 g (85%), m.p. 140°-143° C.; [α]D23 -21.8° (c 0.8 DMF); RfB, 0.85; RfI, 0.62.

Workup

  1. customAfter overnight storage at room temperature a semisolid mass formed
  2. customMost of the solvent was removed in vacuo
  3. customthe residue triturated with EtOAc and with ether
  4. customdried

Sources & evidence

ORD record
ord-6546995932e74ebfb36183f6b1aad909
Source dataset
uspto-grants-1980_12
Patent number
US04237046

Reaction notes

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