Hydrochloric Acid → Boc-Asn-Ala-OBzl

HRID 2419492Notes

Reaction equation

HRID 2419492 reaction equation
Cl.[NH2:2][C@H:3]([C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6])[CH3:4].[NH:15]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C@H:16]([C:21](O)=[O:22])[CH2:17][C:18](=[O:20])[NH2:19].CN1CCOCC1.C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1>CN(C=O)C>[NH:15]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C@H:16]([C:21]([NH:2][C@H:3]([C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6])[CH3:4])=[O:22])[CH2:17][C:18](=[O:20])[NH2:19]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 82035N2-((tert-Butoxy)carbonyl)-L-asparagineHCID 726858benzyl (2S)-2-aminopropanoate

Product 1

HCID 131711194Boc-Asn-Ala-OBzl

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The HCl salt of H-Ala-OBzl (43 g, 200 mmol) was dissolved in DMF (500 ml) and stirred with Boc-Asn-OH (46.5 g, 200 mmol), NMM (27 ml), HOBt (54 g), and DCC (45 g) at 0° C for 1.5 hr and 25° C for 17 hr. The reaction mixture was worked up as in Example 11 to a solid which was crystallized from tetrahydrofuran and minimum petroleum ether: 62.5 g (79.4%); mp 140°-141° C; [α]D25 -31.1° (c 1, MeOH). Anal. Calcd for C19H27N3O6 (393.44): C, 58.00; H, 6.92; N, 10.68. Found: C, 57.77; H, 7.09; N, 10.52.

Workup

  1. customwas crystallized from tetrahydrofuran and minimum petroleum ether

Sources & evidence

ORD record
ord-8a22cbfb8852437ab15cde2e79aef37b
Source dataset
uspto-grants-1978_08
Patent number
US04105652

Reaction notes

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