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

HRID 1732523
Notes
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Reaction equation

HRID 1732523 reaction equation
[CH2:1]([O:8][C:9](=[O:46])[C@H:10]([CH2:31][CH2:32][CH2:33][CH2:34][NH:35][C:36]([O:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[O:37])[NH:11][C:12](=[O:30])[C@H:13]([CH:27]([CH3:29])[CH3:28])[NH:14][C:15](=[O:26])[C@H:16]([CH3:25])NC(OC(C)(C)C)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C([O-])=O.[NH:54]([C:72]([O:74][C:75]([CH3:78])([CH3:77])[CH3:76])=[O:73])[C@H:55]([C:60](OC1C=CC([N+]([O-])=O)=CC=1)=[O:61])[CH2:56][CH2:57][S:58][CH3:59].CC[N:81](C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[CH2:1]([O:8][C:9](=[O:46])[C@H:10]([CH2:31][CH2:32][CH2:33][CH2:34][NH:35][C:36]([O:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[O:37])[NH:11][C:12](=[O:30])[C@H:13]([CH:27]([CH3:28])[CH3:29])[NH:14][C:15](=[O:26])[C@H:16]([CH3:25])[NH:81][C:60](=[O:61])[C@H:55]([CH2:56][CH2:57][S:58][CH3:59])[NH:54][C:72]([O:74][C:75]([CH3:78])([CH3:77])[CH3:76])=[O:73])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 84468TrifluoroacetateHCID 7021880Boc-Met-ONpHCID 131711964t-Butyloxycarbonyl-L-alanyl-L-valyl-Nepsilon-benzyloxycarbonyl-L-lysine benzyl ester

Product 1

HCID 86737377
t-Butyloxycarbonyl-L-methionyl-L-alanyl-L-valyl-Nepsilon-benzyloxycarbonyl-L-lysine benzyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Partial deprotection of compound XXI (3.4 g, 5.3 mmole) was carried out as described in the previous paragraph. The trifluoroacetate salt (RfC, 0.75) was acylated in DMF (50 ml) with Boc-L-Met-ONp (2.18 g, 5.9 mmole, Bachem) in the presence of DIEA (1.9 ml, 12 mmole) and HOBt (0.9 g, 5.9 mmole). After 4 hr at room temperature the reaction was complete. Evaporation of most of the solvent in vacuo was followed by trituration with EtOAc. The precipitate was washed with EtOAc, with ether and dried: 3.8 g (93%); m.p. 169°-171° C., [α]D24 -21.5° (c 1.2, DMF) RfK, 0.65; RfI, 0.52.

Workup

  1. customEvaporation of most of the solvent in vacuo
  2. washThe precipitate was washed with EtOAc, with ether
  3. customdried

Sources & evidence

ORD record
ord-83288b81c18f488c859c673fe04e5fbf
Source dataset
uspto-grants-1980_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04237046

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes