Diisopropylethylamine → HCID 178465080, compound

HRID 2368207Notes

Reaction equation

HRID 2368207 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH:12]([C:14]([OH:34])([PH2:32]=[O:33])[CH:15]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:22][CH:21]=1)[C:16](O)=[O:17])[CH3:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:36][C@H:37]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH3:38].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C>[C:42]([O:41][C:39](=[O:40])[CH:37]([NH:36][C:16](=[O:17])[CH:15]([C:14]([CH:12]([NH:11][C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:10])[CH3:13])([OH:34])[PH2:32]=[O:33])[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)=[CH:22][CH:21]=1)[CH3:38])([CH3:45])([CH3:44])[CH3:43]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 11275390tert-Butyl alaninate hydrochlorideHCID 178465408HCID 178465408, compound

Product 1

HCID 178465080HCID 178465080, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound from step 1 (0.9 g) is solubilised in 10 ml of DMF in nitrogen, and t-butyl alaninate hydrochloride (450 mg), 2.5 ml of DIEA (6 eq) and 1.98 g of TBTU (3 eq) are successively added. The mixture is stirred for 15 min at ambient temperature and the reaction is processed as in step 4 of example 3. 1.10 g of expected product (97%) is obtained.

Sources & evidence

ORD record
ord-23e6596847fd47a29375f0bf66bcaa6d
Source dataset
uspto-grants-2014_04
Patent number
US08703747B2

Reaction notes

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