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Water → HCID 131711688, compound

HRID 2052266
Notes
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Reaction equation

HRID 2052266 reaction equation
[NH2:1][C@H:2]([C:11]([NH:13][C@@H:14]([C:21]([NH2:23])=[O:22])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[CH2:3][C:4](=[O:10])[O:5][C:6]([CH3:9])([CH3:8])[CH3:7].Cl.[NH:25]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[C@H:26]([C:31](ON1C(=O)CCC1=O)=[O:32])[CH2:27][CH2:28][S:29][CH3:30].C(N(CC)CC)C.O>CN(C=O)C.C(O)C>[NH:25]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[C@H:26]([C:31]([NH:1][C@H:2]([C:11]([NH:13][C@@H:14]([C:21]([NH2:23])=[O:22])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[O:12])[CH2:3][C:4](=[O:10])[O:5][C:6]([CH3:7])([CH3:8])[CH3:9])=[O:32])[CH2:27][CH2:28][S:29][CH3:30]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 12876462L-Methionine, N-[(1,1-dimethylethoxy)carbonyl]-, 2,5-dioxo-1-pyrrolidinyl esterHCID 131711685HCID 131711685, compound

Product 1

HCID 131711688HCID 131711688, compoundYield 84.9%

Reagents, catalysts & solvents 2

HCID 702
Ethanol
Solvent
HCID 6228DimethylformamideSolvent

Procedure

5.0 g (14 mmoles) of H-Asp(OtBu)-D-Phg-NH2.HCl, prepared as described in Example 1, Step 4, and 4.85 g (14 mmoles) of BOC-Met-OSu are dissolved in 60 ml of DMF, and 1.96 ml (14 mmoles) of triethylamine are added to the solution. Next day the resulting suspension is evaporated in vacuo, and the residue is isolated with water. The obtained crude product, weighing 7.83 g, is decolourized in 40 ml of hot ethanol, and 40 ml of water are added to the hot solution to precipitate the product. 6.57 g (84%) of BOC-Met-Asp(OtBu)-D-Phg-NH2 are obtained; the chromatographically uniform product melts at 194°-196° C. A sample of the product melts at 197°-198° C. after recrystallization from ethanol. Rf4 =0.75; [α]D =-67.2° (c=1.0, in dimethyl formamide).

Workup

  1. customNext day the resulting suspension is evaporated in vacuo
  2. customthe residue is isolated with water
  3. customThe obtained crude product
  4. customto precipitate the product

Sources & evidence

ORD record
ord-aafd91a8fa884b9498cd382dbc60d7d1
Source dataset
uspto-grants-1980_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04183909

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes