Boc-Dap-OH → HCID 86647135, compound

HRID 2369801Notes

Reaction equation

HRID 2369801 reaction equation
[C:1]([O:5][C:6](=[O:44])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21](=[O:43])[NH:22][CH2:23][C@H:24]([NH:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[C:25]([O:27]N1C(=O)CCC1=O)=O)([CH3:4])([CH3:3])[CH3:2].C(OC(=O)CCCCCCCCCCCCCCC(=O)NCCCC[C@H](NC(OC(C)(C)C)=O)C(ON1C(=O)CCC1=O)=O)(C)(C)C.[NH2:92][CH2:93][C@H:94]([NH:98][C:99]([O:101][C:102]([CH3:105])([CH3:104])[CH3:103])=[O:100])[C:95]([OH:97])=[O:96]>CN(C=O)C>[C:1]([O:5][C:6](=[O:44])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21](=[O:43])[NH:22][CH2:23][C@H:24]([NH:35][C:36]([O:38][C:39]([CH3:40])([CH3:41])[CH3:42])=[O:37])[C:25](=[O:27])[NH:92][CH2:93][C@H:94]([NH:98][C:99]([O:101][C:102]([CH3:105])([CH3:104])[CH3:103])=[O:100])[C:95]([OH:97])=[O:96])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 2755946Boc-Dap-OH2×HCID 86647136HCID 86647136, compoundHCID 86647137HCID 86647137, compound

Product 1

HCID 86647135HCID 86647135, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

15-[(S)-2-tert-Butoxycarbonylamino-2-(2,5-dioxo-pyrrolidin-1-yloxycarbonyl)ethylcarbamoyl]pentadecanoic acid tert-butyl ester can be prepared in similar fashion as that described for 15-[(S)-5-tert-butoxycarbonylamino-5-(2,5-dioxopyrrolidin-1-yloxycarbonyl)pentylcarbamoyl]pentadecanoic acid tert-butyl ester using (S)-3-amino-2-tert-butoxycarbonylamino propionic acid, and it can be reacted with (S)-3-amino-2-tert-butoxycarbonylamino propionic acid in DMF at RT for 16 h. After concentrating under vacuum, AcOEt can be added the residue and the mixture can be washed with 0.2 N HCl. The organic phase is then dried over MgSO4 and concentrated under vacuum to yield the crude product, 15-[(S)-2-tert-butoxycarbonylamino-2-((S)-2-tert-butoxycarbonylamino-2-carboxyethylcarbamoyl)ethylcarbamoyl]pentadecanoic acid tert-butyl ester. This can either be used without further purification or purified by flash chromatography.

Workup

  1. concentrationAfter concentrating under vacuum, AcOEt
  2. additioncan be added the residue
  3. washthe mixture can be washed with 0.2 N HCl
  4. dry with materialThe organic phase is then dried over MgSO4
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-2a437cef76e94a4fb01327df72b71bdf
Source dataset
uspto-grants-2014_04
Patent number
US08710000B2

Reaction notes

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