Benzyloxycarbonylglycine → HCID 69221815, compound

HRID 130380Notes

Reaction equation

HRID 130380 reaction equation
C(OC(C#CCNCC=CCOC(=O)C)=O)(C)(C)C.[C:20]([O:24][C:25]([N:27]1[CH2:31][CH:30]2[CH:32]([CH2:36][O:37][C:38](=[O:40])[CH3:39])[CH:33]([NH2:35])[CH2:34][CH:29]2[CH2:28]1)=[O:26])([CH3:23])([CH3:22])[CH3:21].[CH2:41]([O:48][C:49]([NH:51][CH2:52][C:53](O)=[O:54])=[O:50])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1.C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>C(#N)C>[C:20]([O:24][C:25]([N:27]1[CH2:31][CH:30]2[CH:32]([CH2:36][O:37][C:38](=[O:40])[CH3:39])[CH:33]([NH:35][C:53](=[O:54])[CH2:52][NH:51][C:49]([O:48][CH2:41][C:42]3[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=3)=[O:50])[CH2:34][CH:29]2[CH2:28]1)=[O:26])([CH3:23])([CH3:21])[CH3:22]

Participants

7

Reactant 5

HCID 14349BenzyloxycarbonylglycineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 69221786HCID 69221786, compoundHCID 86760680HCID 86760680, compound

Product 1

HCID 69221815HCID 69221815, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

By sequentially following the procedures of Example 3, Parts B and C, and Example 1, Parts A and B, acetic acid 4-(tert-butoxy-carbonylprop-2-ynylamino)-but-2-enyl ester is converted to 4-acetoxymethyl-5-aminooctahydrocyclopenta[c]pyrrole-2-carboxylic acid tert-butyl ester. A solution of this material and benzyloxycarbonyl glycine in acetonitrile is treated sequentially with diisopropylethylamine and TBTU, and the resulting mixture is stirred at room temperature until the reaction is complete. The mixture is concentrated under vacuum yielding a residue. The residue is purified by flash column chromatography providing the title product.

Workup

  1. concentrationThe mixture is concentrated under vacuum
  2. customyielding a residue
  3. customThe residue is purified by flash column chromatography

Sources & evidence

ORD record
ord-ea57d76ffdb64978a11f45d3a93ad583
Source dataset
uspto-grants-2008_06
Patent number
US07381738B2

Reaction notes

Loading…